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3,4,6-三-氧-苄基-2-脱氧-D-吡喃葡萄糖 | 160549-11-1

分子结构分类

有机化合物 - 有机氧化合物

中文名称

3,4,6-三-氧-苄基-2-脱氧-D-吡喃葡萄糖

中文别名

——

英文名称

3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose

英文别名

3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranose；(4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol；3,4,6-tri-O-benzyl-2-deoxyglucopyranose；3,4,6-tri-O-benzyl-2-deoxy-α,β-D-glucopyranose；(4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol

CAS

160549-11-1

化学式

C₂₇H₃₀O₅

mdl

——

分子量

434.532

InChiKey

PDGHLARNGSMEJE-GWDBROLASA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

104-108°C
沸点：

581.8±50.0 °C(Predicted)
密度：

1.20±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3.9
重原子数：

32
可旋转键数：

10
环数：

4.0
sp3杂化的碳原子比例：

0.33
拓扑面积：

57.2
氢给体数：

1
氢受体数：

5

安全信息

WGK Germany：

3
储存条件：

存储条件：2-8°C，干燥，惰性气体环境中。

SDS

SDS：fb8b55b2175063ca4fc6178eb366acdc

查看

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	methyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-gluco-pyranoside	74545-14-5	C₂₈H₃₂O₅	448.559
甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷	methyl 2,3,4-tri-O-benzyl-D-glucopyranoside	53008-65-4	C₂₈H₃₂O₆	464.558
2,3,5-三-O-(苯基甲基)-D-呋喃阿拉伯糖	2,3,5-tri-O-benzyl-D-arabinofuranose	160549-10-0	C₂₆H₂₈O₅	420.505
——	methyl 2,3,5-tri-O-benzyl-D-arabinofuranoside	89824-86-2	C₂₇H₃₀O₅	434.532
——	(2R,3R,4R)-6,6-bis(methylsulfanyl)-1,3,4-tris(phenylmethoxy)hexan-2-ol	134502-26-4	C₂₉H₃₆O₄S₂	512.734
3,4,6-三苄氧基-D-葡萄烯糖	3,4,6-tri-O-benzyl-D-glucal	55628-54-1	C₂₇H₂₈O₄	416.517

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-gluco-pyranoside	74545-14-5	C₂₈H₃₂O₅	448.559
——	isopropyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranoside	——	C₃₀H₃₆O₅	476.613
——	cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside	82252-31-1	C₃₃H₄₀O₅	516.678
——	cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside	82252-30-0	C₃₃H₄₀O₅	516.678
——	allyl 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside	1095377-23-3	C₃₀H₃₄O₅	474.597
——	Bn(-3)[Bn(-4)][Bn(-6)]2-deoxy-D-araHex(b1-6)[Bn(-3)][Bn(-4)]2-deoxy-D-araHex(a)-O-allyl	1095377-27-7	C₅₀H₅₆O₉	800.989
——	3,4,6-tri-O-benzyl-2-deoxy-β-D-arabinohexopyranosyl hydroperoxide	861100-42-7	C₂₇H₃₀O₆	450.532
——	3,4,6-tri-O-benzyl-2-deoxy-α-D-arabinohexopyranosyl hydroperoxide	216965-18-3	C₂₇H₃₀O₆	450.532
——	methyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside	——	C₅₅H₆₀O₁₀	881.075
——	methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl)-α-D-glucopyranoside	117841-70-0	C₅₅H₆₀O₁₀	881.075
——	methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl)-α-D-glucopyranoside	——	C₅₅H₆₀O₁₀	881.075
——	methyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-α-D-glucopyranoside	——	C₅₅H₆₀O₁₀	881.075
——	methyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside	117841-73-3	C₅₅H₆₀O₁₀	881.075
——	Bn(-3)[Bn(-4)][Bn(-6)]2-deoxy-D-araHex(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Man(a)-O-allyl	1095377-32-4	C₅₇H₆₂O₁₀	907.113
——	O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	79384-22-8	C₃₉H₄₈O₁₀	676.804
——	(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside	79384-19-3	C₃₉H₄₈O₁₀	676.804
——	3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate	220284-26-4	C₂₉H₃₀Cl₃NO₅	578.92
——	3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside	——	C₃₉H₄₈O₁₀	676.804
——	2-naphthyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside	136174-75-9	C₃₇H₃₆O₅	560.69
——	o-cresyl 2-deoxy-3,4,6-tri-O-benzyl-β-D-gluco-pyranoside	136174-88-4	C₃₄H₃₆O₅	524.657
——	(2R,3R,4R)-1,3,4-tris(phenylmethoxy)hept-6-en-2-ol	157736-63-5	C₂₈H₃₂O₄	432.56
——	1-naphthyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside	1448617-49-9	C₃₇H₃₆O₅	560.69
——	2-deoxy-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone	——	C₂₇H₂₈O₅	432.516
——	3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride	163916-60-7	C₂₇H₂₉FO₄	436.523
——	O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-carbobenzyloxy-L-serine methyl ester	1423497-10-2	C₃₉H₄₃NO₉	669.772
——	cholesteryl (3,4,6-tri-O-benzyl-2-deox-β-D-glucopyranoside)	——	C₅₄H₇₄O₅	803.179
——	2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-mannopyranose	339570-33-1	C₂₇H₂₉N₃O₅	475.544
——	3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranosyl benzyl phthalate	779352-72-6	C₄₂H₄₀O₈	672.775
——	1,6-anhydro-4,5,7-tri-O-benzyl-2,3-dideoxy-D-glucosept-1-enitol	592497-14-8	C₂₈H₃₀O₄	430.544
——	2-Deoxy-D-glucose	61-58-5	C₆H₁₂O₅	164.158
——	3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl azide	683788-70-7	C₂₇H₂₉N₃O₄	459.545
——	(2R,3S,4R)-6-octadecylsulfanyl-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane	256390-59-7	C₄₅H₆₆O₄S	703.083
3,4,6-三苄氧基-D-葡萄烯糖	3,4,6-tri-O-benzyl-D-glucal	55628-54-1	C₂₇H₂₈O₄	416.517
——	(2R,3S,4R,6S)-6-(2,4-dinitrophenoxy)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane	1095377-25-5	C₃₃H₃₂N₂O₉	600.625

反应信息

作为反应物：

描述：

3,4,6-三-氧-苄基-2-脱氧-D-吡喃葡萄糖在双(三甲基硅烷基)氨基钾、 2,4,6-三叔丁基嘧啶作用下，以四氢呋喃为溶剂，生成 D-葡萄烯糖

参考文献：

名称：

Reagent-Controlled Stereoselective Glycosylation

摘要：

提供了一种高效立体选择性形成糖苷键的方法，无需使用假体或定向基团。

公开号：

US20150038689A1
作为产物：

描述：

(2R,3R,4R)-6,6-bis(methylsulfanyl)-1,3,4-tris(phenylmethoxy)hexan-2-ol 在 N-溴代丁二酰亚胺(NBS) 、水、三乙基碳酸氢铵缓冲液作用下，以乙腈为溶剂，反应 0.08h，以84%的产率得到3,4,6-三-氧-苄基-2-脱氧-D-吡喃葡萄糖

参考文献：

名称：

Van der Klein; De Nooy; Van der Marel, Synthesis, 1991, # 5, p. 347 - 349

摘要：

DOI：

点击查看最新优质反应信息

文献信息

C-Glycosylation enabled by N-(glycosyloxy)acetamides

作者：Miao Liu、Bo-Han Li、Tian Li、Xia Wu、Meng Liu、De-Cai Xiong、Xin-Shan Ye

DOI：10.1039/d0ob00561d

日期：——

The C-glycosylation of C-nucleophiles including allyltrimethylsilane, silyl enol ethers and phenols with N-(glycosyloxy)acetamides as glycosyl donors has been realized. This protocol provides a convenient and practical route for the synthesis of alkyl C-glycosides and aryl 2-deoxy-β-C-glycosides under mild reaction conditions.

已经实现了包含N-（糖基氧基）乙酰胺作为糖基供体的C-亲核试剂（包括烯丙基三甲基硅烷，甲硅烷基烯醇醚和苯酚）的C-糖基化。该方案为在温和的反应条件下合成烷基C-糖苷和芳基2-脱氧-β-C-糖苷提供了方便实用的途径。
Chemistry of β-trimethylsilylethanol. II. A new method for protection of an anomeric center in pyranosides

作者：Bruce H. Lipshutz、Joseph J. Pegram、Matthew C. Morey

DOI：10.1016/s0040-4039(01)82992-0

日期：1981.1

Protection of the anomeric center in various carbohydrates as a β-trimethylsilylethyl glycoside is reported. The free sugar can be regenerated using LiBF4 in acetonitrile.

据报道，作为β-三甲基甲硅烷基乙基糖苷，各种碳水化合物中的异头异构中心得到保护。可以使用乙腈中的LiBF 4再生游离糖。
A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides

作者：Edward I. Balmond、David Benito-Alifonso、Diane M. Coe、Roger W. Alder、Eoghan M. McGarrigle、M. Carmen Galan

DOI：10.1002/anie.201403543

日期：2014.7.28

disaccharides or glycoconjugates with high α‐selectivity and yields (77–97 %) using a trans‐fused cyclic 3,4‐O‐disiloxane protecting group and TsOH⋅H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side‐chain conformation augments the selectivity.

已经开发出一种实用的方法，使用反式稠合环状 3,4-O-二硅氧烷保护基团和 TsOH⋅H 2 O ，将葡糖和鼠李糖转化为具有高α-选择性和产率（77-97%）的二糖或糖缀合物（ 1 mol%) 作为催化剂。异头选择性的控制来自中间氧杂碳鎓阳离子的构象锁定。Glucals 优于鼠李糖醇，因为 C6 侧链构象增强了选择性。
Additive‐Free Gold(III)‐Catalyzed Stereoselective Synthesis of 2‐Deoxyglycosides Using Phenylpropiolate Glycosides as Donors

作者：Mukta Shaw、Amit Kumar

DOI：10.1002/asia.201900888

日期：2019.12.13

Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields

在无外部添加剂的条件下，使用金（III）盐作为催化剂，可从台式稳定且易于合成的脱氧苯丙酸丙二醇酯（D-PPGs）中实现脱氧糖苷的立体选择性合成。在简单的催化系统下，D-PPG与多种糖和非糖受体反应，以高至优异的收率产生主要的α-立体选择性O / N-脱氧糖苷，并再生易于分离和重用的苯丙酸。在优化的反应条件下，含有武装和解除武装团体的脱氧PPG能够很好地存活。另外，展示了D-PPG的正交性质，并且还合成了1，1'-连接的海藻糖型糖。
Lewis acid–surfactant-combined catalyzed synthesis of 4-aminocyclopentenones from glycals in water

作者：Siming Wang、Ronny William、Kim Kui Georgina Estelle Seah、Xue-Wei Liu

DOI：10.1039/c3gc41032c

日期：——

4-Aminocyclopentenones were synthesized from readily available glycals and secondary anilines, with the aid of a Lewis acidâsurfactant-combined catalyst. The reactions proceeded via a 4Ï conrotatory electrocyclization, affording the corresponding 4-aminocyclopentenones in good yields with excellent diastereoselectivities.

4-氨基环戊烯酮是通过易得的糖醇和次级苯胺在路易斯酸-表面活性剂联合作用催化剂的帮助下合成的。这些反应通过4π共旋转电环化进行，得到相应的4-氨基环戊烯酮，产率良好且具有极好的立体选择性。