benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside | 106445-56-1

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside

英文别名

benzyl 2,3,4-tri-O-benzyl-D-glycero-α-D-manno-heptopyranoside；benzyl 2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside

benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside化学式

CAS

106445-56-1

化学式

C₃₅H₃₈O₇

mdl

——

分子量

570.683

InChiKey

QGJRSQYZNGTTQY-OGHGGVFLSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

715.6±60.0 °C(predicted)
密度：

1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

辛醇/水分配系数(LogP)：

5.04
重原子数：

42.0
可旋转键数：

14.0
环数：

5.0
sp3杂化的碳原子比例：

0.31
拓扑面积：

86.61
氢给体数：

2.0
氢受体数：

7.0

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
——	benzyl 2,3,4-O-tribenzyl-6,7-dideoxy-α-D-hept-6-enopyranoside	1554004-68-0	C₃₅H₃₆O₅	536.668
——	benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside	102046-36-6	C₃₄H₃₄O₆	538.64
——	benzyl 6-O-trityl-α-D-mannopyranoside	77455-30-2	C₃₂H₃₂O₆	512.602
——	3-O-benzyl-5-deoxy-5-C-[benzyl 2,3,4-tri-O-benzyl-7-deoxy-D-glycero-α-D-manno-heptopyranosid-7(E)-ylidene]-1,2-O-isopropylidene-α-D-xylofuranose	253596-65-5	C₅₀H₅₄O₁₀	814.973
——	benzyl 6-O-tetra-butyldiphenylsilyl-2,3,4-O-tribenzyl-α-D-mannopyranoside	1222709-77-4	C₅₀H₅₄O₆Si	779.061
——	benzyl 6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside	114894-82-5	C₂₉H₃₆O₆Si	508.687

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	benzyl 2,3,4,6-O-tetrabenzyl-6-deoxy-glycero-α-D-manno-heptopyranoside	582308-13-2	C₃₅H₃₈O₆	554.683
——	benzyl 7-O-dibenzyl-phosphono-2,3,4-O-tri-benzyl-6-deoxy-glycero-α-D-mannoheptopyranoside	1554005-06-9	C₄₉H₅₁O₉P	814.912
——	benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-6-deoxy-glycero-α-D-mannoheptopyranoside	1554005-00-3	C₅₁H₅₆O₆Si	793.088
——	benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-L-glycero-α-D-mannoheptopyranoside	1554004-89-5	C₅₁H₅₆O₇Si	809.087
——	benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside	1554004-75-9	C₅₁H₅₆O₇Si	809.087
——	D-glycero-D-manno-heptose	1224939-44-9	C₇H₁₄O₇	210.184
——	benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside	1554004-98-6	C₅₈H₆₀O₈SSi	945.261
——	(S)-2-((tert-butyldiphenylsilyl)oxy)-1-((2R,3S,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)tetrahydro-2H-pyran-2-yl)ethyl 4-nitrobenzoate	1588523-50-5	C₅₈H₅₉NO₁₀Si	958.193

反应信息

作为反应物：

描述：

benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside 在咪唑、四氮唑、 4-二甲氨基吡啶、偶氮二异丁腈、四丁基氟化铵、三正丁基氢锡作用下，以四氢呋喃、正己烷、二氯甲烷、 N,N-二甲基甲酰胺、甲苯、乙腈为溶剂，反应 17.5h，生成

参考文献：

名称：

Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE

摘要：

An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-D-glycero-beta-D-mannoheptose (ADP-D, D-heptose) was reported using chemically synthesized D, D-heptose-7-phosphate and the ADP-D, D-heptose biosynthetic enzymes HldE and GmhB. Moreover, the result of investigating substrate specificity of the kinase action of HldE revealed that HldE had highly restricted substrate specificity towards structurally modified heptose-7-phosphate analogs. Published by Elsevier Ltd.

DOI：

10.1016/j.bmc.2013.12.019
作为产物：

描述：

溴甲苯在咪唑、四氧化锇、正丁基锂、四丁基氟化铵、水、 sodium hydride 、戴斯-马丁氧化剂、 N-甲基吗啉氧化物、乙酰氯作用下，以四氢呋喃、正己烷、二氯甲烷、 N,N-二甲基甲酰胺、丙酮、 mineral oil 为溶剂，反应 18.17h，生成 benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside

参考文献：

名称：

Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE

摘要：

An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-D-glycero-beta-D-mannoheptose (ADP-D, D-heptose) was reported using chemically synthesized D, D-heptose-7-phosphate and the ADP-D, D-heptose biosynthetic enzymes HldE and GmhB. Moreover, the result of investigating substrate specificity of the kinase action of HldE revealed that HldE had highly restricted substrate specificity towards structurally modified heptose-7-phosphate analogs. Published by Elsevier Ltd.

DOI：

10.1016/j.bmc.2013.12.019

点击查看最新优质反应信息

文献信息

Application of Sugar Phosphonates for the Preparation of Higher Carbon Monosaccharides

作者：Slawomir Jarosz、Stanislaw Skóra、Artur Stefanowicz、Mateusz Mach、Jadwiga Frelek

DOI：10.1080/07328309908544046

日期：1999.1.1

nucleophilic than corresponding phosphoranes. The sugar enones are reduced to appropriate allylic alcohols with zinc borohydride; the stereoselectivity of this process is >97:3 (with the D-glycero isomer predominating) when the carbonyl group is placed at the α-position to the sugar ring. CD spectroscopy was used for the determination of the configuration of higher sugar allylic alcohols.

摘要糖衍生的膦酸酯[Sug-C（O）CH2P（O）（OMe）2]与糖醛（Sug'-CHO）的反应提供了通式为Sug-C（O）CH = CH-Sug的高级烯酮具有双键的反式构型。膦酸酯方法优于先前使用的膦烷方法[Sug-C（O）CH = PPh3 + Sug'-CHO]，因为糖膦酸酯可以以更高的产率制备并且比相应的膦烷亲核得多。用硼氢化锌将糖烯酮还原为合适的烯丙醇；当羰基位于糖环的α-位置时，此过程的立体选择性> 97：3（D-甘油异构体占主导）。CD光谱法用于确定高级糖烯丙基醇的构型。
New syntheses of d- and l-glycero-d-manno-heptoses

作者：Krzysztof Dziewiszek、Aleksander Zamojski

DOI：10.1016/0008-6215(86)80013-1

日期：1986.8

Abstract Three methods for the synthesis of the title compounds starting from benzyl 2,3,4-tri-O-benzyl-α- d -manno-hexodialdo-1,5-pyranoside (7 have been elaborated. Conversion of 7 into the cyanohydrin followed by reduction to give the amine and then deamination gave a derivative of l -glycero- d -manno-heptose in low yield. Condensation of 7 with 2-methylfuran gave two stereoisomeric 6-C-(2-methyl-5-furyl)

摘要合成了由苄基2,3,4-三-O-苄基-α-d-甘露六己醛-1,5-吡喃糖苷起始的三种标题化合物的合成方法（其中7种已被合成。7种转化为氰醇然后还原得到胺，然后脱氨基得到低产率的1-甘油-d-甘露庚糖衍生物，将7与2-甲基呋喃缩合得到两个立体异构体6-C-（2-甲基-5-呋喃基）。将主要的立体异构体进行臭氧处理，然后还原得到d-甘油-d-甘露庚糖衍生物，将7与烯丙氧基甲基镁氯化物缩合，可得到产率高且l-甘油d-甘油比率高的两种庚糖衍生物。这些衍生物的保护基比为3.2：1。脱保护得到的庚糖产率很高。
Synthesis of L-glycero-D-manno-heptose

作者：G. J. P. H. Boons、P. A. M. van der Klein、G. A. van der Marel、J. H. van Boom

DOI：10.1002/recl.19881070706

日期：——

The easily accessible benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (2) can be converted, in a highly stereoselective manner, by the two-step Tamao method to benzyl 2,3,4-tri-O-benzyl-β-L-glycero-D-manno-heptopyranoside (4a).

易于获得的苄基2,3,4-三-O-苄基-α-D-甘露糖六醛-1,5-吡喃糖苷（2）可以通过两步Tamao方法以高度立体选择性的方式转化为苄基2,3,4-三-O-苄基-β-L-甘油-D-甘露聚糖-七吡喃糖苷（4a）。
Convenient approach to higher carbon sugars. First synthesis of the free C12-sugar: d-erythro-l-manno-d-manno-dodecose

作者：Sławomir Jarosz、Stanisław Skóra、Izabela Kościołowska

DOI：10.1016/s0008-6215(02)00484-6

日期：2003.2

The model synthesis of a C12-aldose was initiated from the easily available dimethyl(benzyl 2,3,4-tri-O-benzyl-alpha-D-manno-heptopyranos-6-ulos-7-yl)phosphonate and 2,3:4,5-di-O-isopropylidene-D-arabinose. (C) 2003 Published by Elsevier Science Ltd.