苄基 2-乙酰氨基-2-脱氧-6-O-三苯基-甲基-alpha-D-吡喃葡萄糖苷 | 33493-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 苄基 2-乙酰氨基-2-脱氧-6-O-三苯基-甲基-alpha-D-吡喃葡萄糖苷
• 中文别名: 苄基2-乙酰氨基-2-脱氧-6-O-三苯甲基-Α-D-吡喃葡萄糖苷；苄基2-乙酰氨基-2-脱氧-6-O-三苯基-甲基-alpha-D-吡喃葡萄糖苷
• 英文名称: benzyl 2-acetamido-2-deoxy-6-O-trityl-α-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-phenylmethoxy-6-(trityloxymethyl)oxan-3-yl]acetamide
• CAS: 33493-71-9
• 化学式: C₃₄H₃₅NO₆
• 分子量: 553.655
• InChiKey: GNACBNSYIVTBNV-UPYFENACSA-N

物化性质

• 熔点：
  99-105 °C
• 沸点：
  623.78°C (rough estimate)
• 密度：
  1.1867 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25,S28A,S37,S45

SDS

Name:	Benzyl 2-Acetamido-2-Deoxy-6-O-Triphenyl- Material Safety Data Sheet
Synonym:	None known
CAS:	33493-71-9

Section 1 - Chemical Product MSDS Name:Benzyl 2-Acetamido-2-Deoxy-6-O-Triphenyl- Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
33493-71-9	Benzyl 2-acetamido-2-deoxy-6-O-triphen	97	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.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.
Antidote: None reported.

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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 agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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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# 33493-71-9: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 103.00 - 105.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C34H35NO6
Molecular Weight: 553.65

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 33493-71-9 unlisted.
LD50/LC50:
Not available.
Not available.
Carcinogenicity:
Benzyl 2-acetamido-2-deoxy-6-O-triphenyl-methyl-1-D-glucopy - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 33493-71-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 33493-71-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 33493-71-9 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：

  苄基 2-乙酰氨基-2-脱氧-6-O-三苯基-甲基-alpha-D-吡喃葡萄糖苷 在 barium dihydroxide 、 boron trifluoride methanol complex 、 barium(II) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 benzyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  在C-9修饰唾液酸的一般方法。N-乙酰基-9-脱氧-9-氟神经氨酸的合成

  摘要：

  将5-乙酰氨基-3,5-二脱氧-2-O-甲基-D-甘油-D-半乳糖-2-壬基吡喃酮酸酯转化为9-O-三苯甲基衍生物，并将剩余的羟基保护为苄基醚。除去三苯甲基，然后用二乙基氨基三氟化硫处理，得到9-脱氧-9-氟衍生物和脱保护的N-乙酰基-9-脱氧-9-氟神经氨酸（8）。在另一种方法中，将2-乙酰氨基-2,6-二脱氧-6-氟-D-吡喃葡萄糖与草酸二叔丁酯钾偶合，然后水解和脱羧，得到8。一些衍生物具有活性作为抑制剂。培养中小鼠乳腺腺癌（TA3）和L1210细胞的生长

  DOI：

  10.1016/0008-6215(88)80153-8
• 作为产物：
  描述：

  三苯基氯甲烷 、 苄基-2-乙酰胺基-2-脱氧-Alpha-D-吡喃葡萄糖苷 以 吡啶 为溶剂， 反应 5.0h， 以86%的产率得到苄基 2-乙酰氨基-2-脱氧-6-O-三苯基-甲基-alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  The Cobalt-Catalyzed Oxygenative Radical Route from Hexopyranosides to Carbapentofuranoses

  摘要：

  DOI：

  10.1002/1099-0690(200009)2000:17<3075::aid-ejoc3075>3.0.co;2-c

文献信息

• A New Synthesis of Benzylidene Acetals
  作者：Chunbao Li、Andrea Vasella

  DOI：10.1002/hlca.19930760115

  日期：1993.2.10

  Aryl-halo-diazirines react under basic conditions with 1,3-cis-, 1,2-cisand 1,2-trans-diols to give acetals. Yields are high. Diastereoselectivities depend upon the diol and upon the reaction conditions. Thus, reaction of the 1,3-cis-diol 1 (Scheme 1) with 2 gave 3 as a single diastereoisomer. The 1,2-cis-diols 4 and 7 led to the endo- and exo-acetals 5/6 (93:7) and 8/9 (ca.10:1), respectively, The

  芳基卤代二嗪在碱性条件下与1,3-顺式，1,2-顺式和1,2-反式-二醇反应生成缩醛。产量高。非对映选择性取决于二醇和反应条件。因此，使1，3-顺-二醇1（方案1）与2反应，得到3为单一非对映异构体。1,2-顺式-diols 4和7导致内切-和外切-acetals 5 / 6（93：7）和8 / 9（CA0.10：1），分别为1,2-反式-diols 10，16，和19与反应2，得到11 / 12（90:10），17 / 18（1：1），和20 / 21（ 6：1）。的（4-硝基苯基）二吖丙因的反应13与10在较高温度下，得到14 / 15（6：4）。尿嘧啶部分，乙酰胺基和烯醇醚部分与反应条件相容。根据涉及烷氧基-卤素交换的反应顺序合理化非对映选择性，该烷氧基-卤素交换具有或不具有区域选择性，随后的烷氧基二嗪热解，烷氧基卡宾的质子化以形成（E）-构型的氧羰基离子和相邻的氧基或羟基，仅对于有限范围的构象异构体是可能的。
• General methods for modification of sialic acid at C-9. Synthesis of N-acetyl-9-deoxy-9-fluoroneuraminic acid
  作者：Moheswar Sharma、Charles R. Petrie、Walter Korytnyk

  DOI：10.1016/0008-6215(88)80153-8

  日期：1988.4

  groups were protected as benzyl ethers. Removal of the trityl group, followed by treatment with diethylaminosulfur trifluoride gave the 9-deoxy-9-fluoro derivative, and deprotection N-acetyl-9-deoxy-9-fluoroneuraminic acid (8). In another procedure, coupling of 2-acetamido-2,6-dideoxy-6-fluoro-D-glucopyranose with potassium di(tert-butyl) oxaloacetate, followed by hydrolysis and decarboxylation gave

  将5-乙酰氨基-3,5-二脱氧-2-O-甲基-D-甘油-D-半乳糖-2-壬基吡喃酮酸酯转化为9-O-三苯甲基衍生物，并将剩余的羟基保护为苄基醚。除去三苯甲基，然后用二乙基氨基三氟化硫处理，得到9-脱氧-9-氟衍生物和脱保护的N-乙酰基-9-脱氧-9-氟神经氨酸（8）。在另一种方法中，将2-乙酰氨基-2,6-二脱氧-6-氟-D-吡喃葡萄糖与草酸二叔丁酯钾偶合，然后水解和脱羧，得到8。一些衍生物具有活性作为抑制剂。培养中小鼠乳腺腺癌（TA3）和L1210细胞的生长
• Modifications at C-3 and C-4 of 2-amino-2-deoxy-d-glucose
  作者：Moheswar Sharma、Walter Korytnyk

  DOI：10.1016/s0008-6215(00)85130-7

  日期：1980.2

  Modifications at C-3 and C-4 of 2-amino-2-deoxy-D-glucose have been developed. A 3,4-double bond was introduced into benzyl 2-acetamido-2-deoxy-3,4-di-O-methylsulfonyl-alpha-D-glucopyranoside by treatment with NaI and Zn. Epoxidation of the double bond with m-chloroperoxybenzoic acid gave an exo-epoxide exclusively. The stereochemistry of the epoxidation product has been confirmed by an alternative

  已经开发了2-氨基-2-脱氧-D-葡萄糖在C-3和C-4的修饰。通过用NaI和Zn处理，将3，4-双键引入到苄基2-乙酰胺基-2-脱氧-3，4-二-O-甲基磺酰基-α-D-吡喃葡萄糖苷中。双键与间氯过氧苯甲酸的环氧化只产生一个外环氧化物。环氧化产物的立体化学已通过另一种合成方法得到证实。1H-nmr光谱分析表明3,4-不饱和衍生物和环氧化物都存在于OH1（D）构象中。亲核试剂（F-，I-）打开3，4-环氧化物，得到具有D-gulo构型的4-取代的衍生物。因此，2-乙酰氨基-1,3,6-三-O-乙酰基-2,4-二脱氧-4-碘-α-D-戊吡喃糖和2-乙酰氨基-1,3,6-三-O-乙酰基-已经合成了3，4-二脱氧-4-氟-α-D-吡喃葡萄糖。关键中间体中的双键还原并脱保护得到2-乙酰氨基-2,3,4-三苯氧基-D-吡喃葡萄糖。一些衍生物具有活性，可在培养物中抑制小鼠乳腺腺癌细胞的生长。
• Preparation of the 3,4-di-O-benzyl and 3,4-di-O-(4-phenylbenzyl) derivatives of benzyl 2-acetamido-2-deoxy-χ-d-glucopyranoside
  作者：Dominicus J.M. van der Vleugel、Johannes F.G. Vliegenthart

  DOI：10.1016/s0008-6215(00)81864-9

  日期：1982.7
• SHARMA, MOHESWAR;PETRIE, CHARLES R. , III;KORYTNYK, WALTER, CARBOHYDR. RES., 175,(1988) N 1, 25-34
  作者：SHARMA, MOHESWAR、PETRIE, CHARLES R. , III、KORYTNYK, WALTER

  DOI：——

  日期：——