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dimethyl (methyl 2,3,4-tri-O-benzyl-D-gluco-heptopyranos-6-ulos-7-yl)phosphonate | 220172-55-4

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

dimethyl (methyl 2,3,4-tri-O-benzyl-D-gluco-heptopyranos-6-ulos-7-yl)phosphonate

英文别名

2-dimethoxyphosphoryl-1-[(2S,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]ethanone

dimethyl (methyl 2,3,4-tri-O-benzyl-D-gluco-heptopyranos-6-ulos-7-yl)phosphonate化学式

CAS

220172-55-4

化学式

C₃₁H₃₇O₉P

mdl

——

分子量

584.603

InChiKey

UPFWYQIWBFCVLZ-SAEUYMBFSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

679.1±55.0 °C(predicted)
密度：

1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

辛醇/水分配系数(LogP)：

3.2
重原子数：

41
可旋转键数：

15
环数：

4.0
sp3杂化的碳原子比例：

0.39
拓扑面积：

98.8
氢给体数：

0
氢受体数：

9

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 (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate	55610-71-4	C₂₉H₃₂O₇	492.569
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

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(E)-3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(2S,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]prop-2-en-1-one	220172-57-6	C₄₀H₄₈O₁₀	688.815
——	methyl 2,3,4,9,10,11-hexa-O-benzyl-7,8-dideoxy-7,8-didehydro-12,13-O-isopropylidene-α-D-gluco-D-gluco-tridec-7(E)-eno-1,5-pyranosid-6-ulose	1049006-95-2	C₅₉H₆₄O₁₁	949.151
——	(E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenone	220172-62-3	C₄₁H₄₈O₁₁	716.826
——	methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside	103597-20-2	C₂₉H₃₄O₇	494.585
——	(2R,3R,4S,5S,6R,7R)-7-[(2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-5,6,7-tris(phenylmethoxy)heptane-1,2,3,4-tetrol	220172-74-7	C₅₅H₆₂O₁₂	915.09
——	(2R,3S,4S,5R,6S)-2-[(1R,2R,3S,4S,5R,6R)-1,2,3,4,5,6,7-heptakis(phenylmethoxy)heptyl]-6-methoxy-3,4,5-tris(phenylmethoxy)oxane	220172-76-9	C₈₃H₈₆O₁₂	1275.59
——	(1R,2R,3R)-1-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[(2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-3-phenylmethoxypropane-1,2-diol	220172-60-1	C₄₇H₅₈O₁₂	814.97
——	methyl 2,3,4,6,7,8-hexa-O-benzyl-9,10:11,12-di-O-isopropylidene-α-L-erythro-L-manno-D-gluco-1,5-pyranoside	1054655-44-5	C₆₁H₇₀O₁₂	995.22
——	(1R,2S,3R)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2,3-triol	——	C₄₁H₅₂O₁₃	752.856
——	(1R,2R,3R)-3-Benzyloxy-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol	220172-94-1	C₄₈H₅₈O₁₃	842.981
——	(E,1R)-3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]prop-2-en-1-ol	220172-58-7	C₄₀H₅₀O₁₀	690.831
——	(E)-(R)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol	220172-63-4	C₄₁H₅₀O₁₁	718.841
——	(2R,3S,4S,5R,6S)-2-[(E,1R)-3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylmethoxyprop-2-enyl]-6-methoxy-3,4,5-tris(phenylmethoxy)oxane	220172-59-8	C₄₇H₅₆O₁₀	780.956
——	(3aR,5R,5aS,8aS,8bR)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran	220172-91-8	C₄₈H₅₆O₁₁	808.966

反应信息

作为反应物：

描述：

dimethyl (methyl 2,3,4-tri-O-benzyl-D-gluco-heptopyranos-6-ulos-7-yl)phosphonate 在 zinc(II) tetrahydroborate 、 18-冠醚-6 、 potassium carbonate 作用下，以乙醚、甲苯为溶剂，反应 16.5h，生成 (E,1R)-3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]prop-2-en-1-ol

参考文献：

名称：

合成高碳糖中的膦酸酯与膦烷方法。D-赤型-L-甘露糖-D-葡萄糖-十二烷醇的制备

摘要：

通过使C 7-膦烷1或C 7-膦酸酯2和13与C 5-或C 6-糖醛偶合而获得高级糖（C 12和C 13）二糖前体5、10和15 。通过（i）用硼氢化锌立体选择性地还原羰基，然后（ii）将所得的烯丙基醇进行甲磺酰化，从而将这些化合物转化为更高的二元醇。一这些衍生物的-化合物8a -被转换成d -赤-大号-甘露- d -葡糖-dodecitol 23上0.5g的规模。

DOI：

10.1039/a807190j
作为产物：

描述：

methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate 、甲基膦酸二甲酯在正丁基锂作用下，生成 dimethyl (methyl 2,3,4-tri-O-benzyl-D-gluco-heptopyranos-6-ulos-7-yl)phosphonate

参考文献：

名称：

合成高碳糖中的膦酸酯与膦烷方法。D-赤型-L-甘露糖-D-葡萄糖-十二烷醇的制备

摘要：

通过使C 7-膦烷1或C 7-膦酸酯2和13与C 5-或C 6-糖醛偶合而获得高级糖（C 12和C 13）二糖前体5、10和15 。通过（i）用硼氢化锌立体选择性地还原羰基，然后（ii）将所得的烯丙基醇进行甲磺酰化，从而将这些化合物转化为更高的二元醇。一这些衍生物的-化合物8a -被转换成d -赤-大号-甘露- d -葡糖-dodecitol 23上0.5g的规模。

DOI：

10.1039/a807190j

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文献信息

Synthesis of Sugar-Derived 2′- and 3′-Substituted Furans and Their Application in Diels−Alder Reactions

作者：Sławomir Jarosz、Mateusz Mach、Katarzyna Szewczyk、Stanisław Skóra、Zbigniew Ciunik

DOI：10.1002/1099-0690(200108)2001:15<2955::aid-ejoc2955>3.0.co;2-0

日期：2001.8

A convenient synthesis of 2′- and 3′-furyl sugars in which the furan and the sugar parts are directly connected is presented. The key step comprises HF·py-induced cyclization of α,β-unsaturated carbonyl compounds (ketones or aldehydes) possessing terminal hydroxymethylene groups protected as TBDPS ethers. Treatment of such furan derivatives with N-phenylmaleimide under high-pressure conditions (11

提出了一种2'-和3'-呋喃糖的便捷合成方法，其中呋喃和糖部分直接相连。关键步骤包括HF·py诱导的具有被保护为TBDPS醚的末端羟基亚甲基的α，β-不饱和羰基化合物（酮或醛）的环化反应。在高压条件下（11 kbar）用N-苯基马来酰亚胺处理此类呋喃衍生物可生成相应的[4 + 2]加合物，其中内型占主导。然而，在p = 1 atm和T = 20°C时，形成了exo异构体作为主要产物。[4 + 2]加合物在升高的温度和大气压下进行逆狄尔斯-阿尔德反应。
Synthesis and Structural Analysis of Higher Analogs of Sucrose

作者：Slawomir Jarosz、Mateusz Mach、Jadwiga Frelek

DOI：10.1080/07328300008544111

日期：2000.1

Three sucrose monoalcohols with free hydroxyl groups at C-1', C-6, and C-6' (1, 4, and 6) were prepared selectively and in good yield from 2,3,3',4,4'-penta-O-benzylsucrose. These compounds were oxidized to aldehydes and reacted with stabilized ylide, Ph3P=CHCO2Me to afford appropriate α,β-unsaturated esters 10, 11, and 12. Each olefin was cis-hydroxylated with OsO4/NMO to stereoisomeric diols 13/14

选择性地制备了三种在C-1'，C-6和C-6'（1、4和6）具有游离羟基的蔗糖一元醇，从2,3,3'，4,4'-五-O-苄基蔗糖。这些化合物被氧化成醛，并与稳定的叶立德（Ph 3 P = CHCO 2 Me）反应，得到适当的α，β-不饱和酯10、11和12。将每种烯烃用OsO 4 / NMO顺式羟基化为立体异构二醇13 / 14、15 / 16和17/18，其配置通过化学相关性和CD评估进行分配。osmylation反应的立体选择性极低（大约3：2），特别是与对6,7-不饱和甲基糖苷的简单衍生物进行的类似过程相比，其异构二醇的比例为10：1。11（在葡萄糖部分由C 2-单元同源的衍生物）的osmylation没有服从Kishi法则。蔗糖醛7与糖衍生的膦酸酯22的霍纳-埃蒙斯反应得到α，β-不饱和衍生物24，其在葡萄糖末端被C 7-单元同源。
The synthesis of higher carbon sugars: a study on the rearrangement of higher sugar allylic alcohols

作者：Mykhaylo A. Potopnyk、Piotr Cmoch、Maciej Cieplak、Agnieszka Gajewska、Sławomir Jarosz

DOI：10.1016/j.tetasy.2011.04.021

日期：2011.4

The C12 higher sugar enone 15 (prepared from the corresponding phosphonate and aldehyde) was highly stereoselectively reduced to the D-glycero-allylic alcohol. The epimeric L-glycero-isomer was obtained by the non-selective reduction of the higher enone under Luche conditions. The separate treatment of both allylic alcohols with triflic anhydride provided the corresponding triflates, which in situ underwent allylic rearrangement with the elimination of one of the benzyl groups (from the aldehyde part of the molecule). The stereochemical aspects of this transformation are also discussed. (C) 2011 Elsevier Ltd. All rights reserved.
Jarosz, Sławomir; Mach, Mateusz; Skóra, Staniław, Synlett, 1999, # 3, p. 313 - 314

作者：Jarosz, Sławomir、Mach, Mateusz、Skóra, Staniław

DOI：——

日期：——
Synthesis of higher carbon sugars. Unexpected rearrangement of higher sugar allylic alcohols

作者：Slawomir Jarosz、Agnieszka Gajewska、Roman Luboradzki

DOI：10.1016/j.tetasy.2008.05.010

日期：2008.6

Coupling of a sugar phosphonate with a sugar aldehyde afforded a C-13-higher sugar enone. Reduction of the carbonyl function provided both stereoisomeric allylic alcohols. Inversion of the configuration at the carbinol centre in these derivatives did not yield the expected S(N)2 product, but proceeded with rearrangement to the tetrahydrofuran derivative. (C) 2008 Published by Elsevier Ltd.