2,3,4,6-四-o-苄基-d-半乳糖吡喃糖苷甲酯 | 195827-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,3,4,6-四-o-苄基-d-半乳糖吡喃糖苷甲酯
• 中文别名: 甲基2,3,4,6-四-O-苄基-D-吡喃半乳糖苷
• 英文名称: methyl 2,3,4,6-tetra-O-benzyl-D-galactopyranoside
• 英文别名: methyl 2,3,4,6-tetra-O-benzyl-D-galactoside；1-O-methyl-2,3,4,6-tetra-O-benzyl-D-galactopyranose；Methyl-2,3,4,6-tetra-O-benzyl-galactopyranoside；(3R,4S,5S,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 195827-82-8
• 化学式: C₃₅H₃₈O₆
• 分子量: 554.683
• InChiKey: IXEBJCKOMVGYKP-KUTUMLQASA-N

物化性质

• 沸点：
  584.38°C (rough estimate)
• 密度：
  1.0612 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25

SDS

Name:	Methyl-2 3 4 6-tetra-O-benzyl-D-galactopyranoside Material Safety Data Sheet
Synonym:	None Known
CAS:	195827-82-8

Section 1 - Chemical Product MSDS Name:Methyl-2 3 4 6-tetra-O-benzyl-D-galactopyranoside Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
195827-82-8	Methyl-2,3,4,6-tetra-O-benzyl-D-galact	ca. 100	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 195827-82-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C35H38O6
Molecular Weight: 554.69

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 195827-82-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl-2,3,4,6-tetra-O-benzyl-D-galactopyranoside - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 195827-82-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 195827-82-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 195827-82-8 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-o-苄基-d-半乳糖吡喃糖苷甲酯 在 三乙基硅烷 、 cerium(III) chloride 、 硫酸 、 三氟化硼乙醚 、 乙酸酐 、 溶剂黄146 、 二甲基亚砜 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol
  参考文献：
  名称：

  X-Ray Crystal Structure Determinations of Galactosylacetylene Building Blocks

  摘要：

  We report the crystal structures of two galactosylacetylenes: 3,7-anhydro-4,5,6,8-tetra- O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mann ooctitol (7) and 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol (8). A short overview of the synthetic chemistry used to obtain these targets is mentioned.

  DOI：

  10.1080/07328303.2011.554935
• 作为产物：
  描述：

  在 盐酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 2,3,4,6-四-o-苄基-d-半乳糖吡喃糖苷甲酯
  参考文献：
  名称：

  Gold-catalysed glycosylation reaction using an easily accessible leaving group

  摘要：

  已经实现了为金催化糖基化开发简单的脱离基团。

  DOI：

  10.1039/c5ob00248f

文献信息

• Highly (<i>Z</i>)-Diastereoselective Synthesis of Trifluoromethylated <i>exo</i>-Glycals via Photoredox and Copper Catalysis
  作者：Christophe J.-M. Frédéric、Jérôme Cornil、Mathilde Vandamme、Lidia Dumitrescu、Abdellatif Tikad、Raphaël Robiette、Stéphane P. Vincent

  DOI：10.1021/acs.orglett.8b02891

  日期：2018.11.2

  Highly (Z)-diastereoselective approaches for the synthesis of trifluoromethylated exo-glycals by copper and photoredox catalysis are described. These complementary reactions are applicable to a wide range of methylene exo-glycals generated from the corresponding pyranoses and furanoses and give trifluoromethylated compounds under mild conditions in moderate to good yields. DFT calculations have allowed

  高度（Ž）用于合成三氟甲基化的方法-diastereoselective外型由铜和photoredox催化-glycals中描述。这些互补反应适用于由相应的吡喃糖和呋喃糖酶产生的各种亚甲基外糖，并在温和的条件下以中等至良好的收率得到三氟甲基化的化合物。DFT计算已使观察到的（Z）-立体选择性合理化。
• NOVEL GEM-DIFLUORINATED C-GLYCOSIDE COMPOUNDS DERIVED FROM PODOPHYLLOTOXIN, THEIR PREPARATION AND THEIR APPLICATIONS
  申请人：Quirion Jean-Charles

  公开号：US20090318675A1

  公开（公告）日：2009-12-24

  The invention relates to a gem-difluoride glycoconjugated compound with formula (I): where R represents II or a benzyl, acetyl, benzoyl alkyl group, R 1 and R 2 may be identical or different and represent H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyldiphenylsilyl protective group or an acetal group of the CR′R′ type, where R′ and R′ may be identical or different and represent H or an alkyl, aryl, benzyl or thiophene group, R 3 represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, R 4 represents OR″, NGR′GR′, N 3 , or a phthalimide, where R″ represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, GR′ and GR′ may be identical or different and represent II or an alkyl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl or benzyloxycarbonyl group, R 5 represents a free or protected hydroxyl group or a halogen, R 6 represents H or an alkyl, acetyl, benzyl, PO 3 H or PO 3 Na group. It is applicable to the preparation of compounds that can be used particularly for the treatment of cancer.

  这项发明涉及一种具有化学式(I)的双氟甘露聚糖结合化合物，其中R代表II或苄基、乙酰基、苯甲酰基烷基，R1和R2可以相同也可以不同，代表H或烷基、苄基、苯甲酰基、乙酰基、戊酰基、三烷基硅基、叔丁基二苯基硅基保护基或CR′R′型的缩醛基团，其中R′和R′可以相同也可以不同，代表H或烷基、芳基、苄基或噻吩基，R3代表H或烷基、苄基、苯甲酰基、乙酰基、戊酰基、三烷基硅基或叔丁基二苯基硅基保护基，R4代表OR″、NGR′GR′、N3或邻苯二甲酰亚胺，其中R″代表H或烷基、苄基、苯甲酰基、乙酰基、戊酰基、三烷基硅基或叔丁基二苯基硅基保护基，GR′和GR′可以相同也可以不同，代表II或烷基、苄基、苯甲酰基、乙酰基、烷氧羰基、烯丙氧羰基或苄氧羰基，R5代表自由或受保护的羟基或卤素，R6代表H或烷基、乙酰基、苄基、PO3H或PO3Na基团。该发明适用于制备特别用于癌症治疗的化合物。
• Phospholipid-saccharide conjugates
  申请人：Genzyme Corporation

  公开号：US05354853A1

  公开（公告）日：1994-10-11

  Novel phospholipid-saccharide conjugates are produced by the reaction of a phospholipid derivative and an activated saccharide. The resulting conjugates can be used to make liposomes which are target-specific or resistant to degradation in vivo.

  新型磷脂酰类和糖醛酸盐结合物通过磷脂酰类衍生物和活性糖醛酸盐的反应制备而成。所得的结合物可用于制备靶向特异性或体内抗降解的脂质体。
• Synthesis of an artificial glycoconjugate polymer carrying P k -antigenic trisaccharide and its potent neutralization activity against Shiga-like toxin
  作者：Hirofumi Dohi、Yoshihiro Nishida、Mitsuharu Mizuno、Masashige Shinkai、Takeshi Kobayashi、Tae Takeda、Hirotaka Uzawa、Kazukiyo Kobayashi

  DOI：10.1016/s0968-0896(99)00129-7

  日期：1999.9

  Fluorescence-labeled glycoconjugate polymers carrying carbohydrate segments of a globotriaosyl ceramide (Gb3) were synthesized and subjected to biological assays using Escherichia coli O-157 strains and Shiga-like toxins (Stx-I and Stx-II). For the fluorescence labeling, a new polymerizable fluorescent monomer with a TBMB carbonyl chromophore (Ex. 325 nm, Em. 410 nm) was designed. A glycosyl monomer of the trisaccharide segment of Gb3 was prepared from p-nitrophenyl beta-lactoside and copolymerized with acrylamide and the fluorescent monomer to prepare a fluorescence-labeled glycoconjugate copolymer carrying [alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl]-(1-->4)-beta- D-glucopyranoside. The polymer showed potent neutralization activity against Stx-I and also binding activity onto E. coli O-157 strains.
• Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile
  作者：Tetsuya Toba、Kenji Murata、Junko Futamura、Kyoko Nakanishi、Bitoku Takahashi、Naohiro Takemoto、Minako Tomino、Takashi Nakatsuka、Seiichi Imajo、Megumi Goto、Takashi Yamamura、Sachiko Miyake、Hirokazu Annoura

  DOI：10.1016/j.bmc.2012.03.025

  日期：2012.5

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.