3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside | 70147-50-1

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

3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside

英文别名

2,3-O-isopropylidene-β-D-erythro-apiofuranose；2,3-O-isopropylidene-β-D-apiofuranose；(3R)-O²,O³-isopropylidene-β-D-apiofuranose；(3aR,6R,6aR)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-6-ol

3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside化学式

CAS

70147-50-1

化学式

C₈H₁₄O₅

mdl

——

分子量

190.196

InChiKey

QCNHIMWAKKHAFC-SHYZEUOFSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

327.1±42.0 °C(Predicted)
密度：

1.313±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-1.2
重原子数：

13
可旋转键数：

1
环数：

2.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

68.2
氢给体数：

2
氢受体数：

5

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
——	2-C-(Hydroxymethyl)-2,3:5,6-di-O-isopropyliden-D-mannofuranose	91738-34-0	C₁₃H₂₂O₇	290.313
——	2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose	91738-34-0	C₁₃H₂₂O₇	290.313
——	2,3:5,6-di-O-isopropylidene-D-mannofuranose	——	C₁₂H₂₀O₆	260.287
——	2,3:5,6-di-O-isopropylidene-α-D-mannofuranose	14131-84-1	C₁₂H₂₀O₆	260.287

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	5-O-benzoyl-2,3-O-isopropylidene-D-apiofuranose	——	C₁₅H₁₈O₆	294.304
——	methyl (β-L-rhamnopyranosyloxymethyl)-(1->3)-C-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-(1->2)-(methyl 3,4-O-isopropylidene-α-D-galactopyranoside)uronate	1334532-95-4	C₂₂H₃₆O₁₅	540.519
——	methyl (2,3-O-isopropylidene-β-D-erythrofuranosyl)-(1->2)-(methyl 3,4-O-isopropylidene-α-D-galactopyranoside)uronate	1334533-10-6	C₁₉H₃₀O₁₁	434.441
——	1,3'-di-O-benzoyl-2,3-O-isopropylidene-D-apio-β-D-furanose	185312-45-2	C₂₂H₂₂O₇	398.412
——	D-apiose	639-97-4	C₅H₁₀O₅	150.131
——	3-(C-hydroxymethyl)-β-D-erythrofuranose	20230-73-3	C₅H₁₀O₅	150.131
——	3-(C-hydroxymethyl)-β-L-threofuranose	30912-14-2	C₅H₁₀O₅	150.131
——	3-(C-hydroxymethyl)-α-D-erythrofuranose	30738-01-3	C₅H₁₀O₅	150.131
——	(3aS,4R,6aR)-6a-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester	191805-00-2	C₁₀H₁₆O₆	232.233

反应信息

作为反应物：

描述：

3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside 在三氟乙酸作用下，反应 12.0h，以76%的产率得到D-apiose

参考文献：

名称：

3-C-（羟甲基）赤藓糖醇和3-C-甲基赤藓糖醇的合成

摘要：

由3-C-（羟甲基）-2,3-O-异亚丙基-D-赤型-四呋喃糖（4）通过水解然后还原，或通过还原然后水解来制备3-C-（羟甲基）赤藓糖醇。4的单甲苯磺酰化，然后用氢化铝锂还原并水解，得到3-C-甲基赤藓糖醇。

DOI：

10.1016/0008-6215(84)85201-5
作为产物：

描述：

2,3:4,5-二-O-(1-甲基乙亚基)-D-木糖在 sodium hydroxide 、 sodium periodate 、溶剂黄146 作用下，以乙醇、水为溶剂，反应 48.5h，生成 3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside

参考文献：

名称：

Triterpenoid saponins from Becium grandiflorum var. obovatum

摘要：

Two new triterpenoid saponins, beciumecine I and 2, were-isolated from the root bark of Becium grandiflorum var, obovatum and their structures established as 3-O-(beta-D-glucopyranosyl) terminolic acid 28-O-beta-D-apiofuranosyl( 1-3)-[alpha-L-rhamnopyranosyl( 1-3)-beta-D-xylopyranosyl( 1-4)]-alpha-L-rhamnopyranosyl(1-2)-alpha-L-arabinopyranoside and 3-O-(beta-D-glucopyranosyl) 24-hydroxyterminolic acid 28-O-alpha-L-rhamnopyranosyl(1-3)-beta-D-xylopyranosyl(1-4)-alpha-L-rhamnopyranosyl(1-2)-alpha-L-arabinopyranoside, respectively. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0031-9422(98)00413-0

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文献信息

An expeditious route to the synthesis of kelampayosides A and B

作者：Howard I. Duynstee、Martijn C. de Koning、Gijs A. van der Marel、Jacques H. van Boom

DOI：10.1016/s0040-4020(99)00527-x

日期：1999.8

Chemoselective NIS/ cat. TfOH-mediated glycosylation of ethyl2,3,4-tri-O-benzoyl-1-thio-β-d-glucopyranoside (13) with ethyl2,3-di-O-acetyl-5-O-benzyl-1-thio-αβ-d-erythro-apiofuranoside (4a) gave dimer14 in an excellent yield. BF3•Et2O-catalysed condensation of the α-trichloroacetimidate31, accessible in two steps from14, with 3,4,5-trimethoxyphenol gave β-linked derivative32 followed by deprotection

化学选择性NIS /猫。TfOH介导的乙基2,3,4-三-O-苯甲酰基-1-硫代-β-d-吡喃葡萄糖苷（13）与乙基2,3-二-O-乙酰基-5-O-苄基-1-硫代-的糖基化作用αβ-d-赤型-呋喃呋喃糖苷（4a）以优异的产率得到二聚体14。BF 3 •Et 2 O催化的α-三氯乙酰亚胺酸酯31的缩合反应（从14步可分两个步骤进行）与3,4,5-三甲氧基苯酚生成β-连接的衍生物32，然后脱保护得到KelampayosideA。保护基的操作为32和所得的后续caffeoylation 36接着进行脱保护，得到Kelampayoside B.图选项
Synthèses de 6-O-β-d-apiofuranosyl-β-d-glucopyranosides de monoterpényle

作者：Oubadjim Mbaïraroua、Thang Ton-That、Claude Tapiéro

DOI：10.1016/0008-6215(94)80057-x

日期：1994.2

benzyl and 2-phenylethyl as aglycon moiety were prepared using the stereospecific trichloroacetimidate Schmidt method. The key intermediate diholoside 1,2,3,4-tetra-O-acetyl-6-O-[(3-C-acetoxymethyl)-2,3-di-O-acetyl-β- d -erythrofuranosyl)-β- d -glucopyranose was obtained by Kochetkov glycosylation of a branched-chain tetrofuranose cyanoethylidene derivative. The NMR data (1H and 13C) of the synthetic compounds

摘要具有（S）-3,7-二甲基-1,6-辛二烯-3-基（芳樟基）的合成apiosyl-glucosides；（R）-1-甲基-1-（4-甲基-3-环己烯-1-基）乙基（松油酰基）；（E）和（Z）-3,7-二甲基-2,6-辛二烯-1-基（香叶基和神经基）；（S）-3,7-二甲基-6-辛烯-1-基（香茅基）；使用立体特异性三氯乙酰亚胺酸酯Schmidt方法制备了作为糖苷配基的苄基和2-苯乙基。关键中间体二乙醇苷1,2,3,4-四-O-乙酰基-6-O-[（3-C-乙酰氧基甲基）-2,3-二-O-乙酰基-β-d-呋喃呋喃糖基）-β- d-吡喃葡萄糖是通过科奇特科夫对支链的四呋喃糖氰基亚乙基衍生物进行糖基化而获得的。报道了合成化合物的NMR数据（1H和13C）和apiose部分的糖基化位移。
Total synthesis of viscumneoside III of Viscum coloratum

作者：Lei Zou、Zixue Zhang、Xiaowen Chen、Hua Chen、Yi Zhang、Jianqi Li、Yu Liu

DOI：10.1016/j.tet.2018.03.057

日期：2018.5

The first total synthesis of viscumneoside III, a promising anti-angina pectoris dihydroflavone O-glycoside isolated from Viscum coloratum was described here. Trichloroaceti-midate was employed as the apiofuranosyl donor to construct the key building block of homoeriodictyol-7-O-β-d-apiosyl-(1 → 2)-β-D-glycoside (1). The longest linear sequence (from 2 to 1) in the synthetic route required thirteen

此处描述了从负鼠Viscum coloratum分离出的一种有前途的抗心绞痛二氢黄酮O-糖苷，即viscumneoside III的第一个全合成。用三氯乙酰胺-氨基甲酸酯作为呋喃呋喃糖基供体来构建高柔顺丁烯醇-7 - O - β - d - apiosyl-（1→2）-β-D-糖苷（1）的关键结构单元。合成路线中最长的线性序列（从2到1）需要13个步骤，最终产物1的总收率为6.3％。
Synthesis of apiose-containing oligosaccharide fragments of the plant cell wall: fragments of rhamnogalacturonan-II side chains A and B, and apiogalacturonan

作者：Sergey A. Nepogodiev、Margherita Fais、David L. Hughes、Robert A. Field

DOI：10.1039/c1ob05587a

日期：——

Fragments of pectic polysaccharides rhamnogalacturonan-II (RG-II) and apiogalacturonan were synthesised using p-tolylthio apiofuranoside derivatives as key building blocks. Apiofuranose thioglycosides can be conveniently prepared by cyclization of the corresponding dithioacetals possessing a 2,3-O-isopropylidene group, which is required for preservation of the correct (3R) configuration of the apiofuranose

果胶多糖rhamnogalacturonan-II (RG-II) 和apiogalacturonan 的片段是使用p- tolylthio apiofuranoside 衍生物作为关键构建块合成的。硫代呋喃糖苷可以通过相应的具有 2,3- O-异亚丙基的二硫代缩醛的环化来方便地制备，这是保持apiofuranose 环的正确 ( 3R ) 构型所必需的。这种保护基团在吡呋喃糖衍生物中的显着稳定性需要用更具反应性的保护基团替换，例如用于合成三糖 β-Rha p -(1→3')-β-Api f -的亚苄基缩醛- (1→2)-α-GalA p-OMe。该三糖的受保护前体的 X 射线晶体结构已被阐明。
Addition of an Apiosyl Radical to Activated Olefins - Synthesis of C-Apiosyl Compounds

作者：Martina Drescher、Friedrich Hammerschmidt

DOI：10.1055/s-1996-4407

日期：1996.12

3’-O-Benzoyl-2,3-O-isopropylidene-D-apio-Î²-D-furanosyl bromide (8), prepared in two steps from 2,3-O-isopropylidene-D-apio-Î²-D-furanose (6), was reacted with tris(trimethylsilyl)silane/AIBN in the presence of an excess of a variety of activated olefins such as dimethyl maleate, methyl acrylate, acrylonitrile, methyl vinyl ketone, crotonaldehyde, cyclopent-2-enone, and cyclohex-2-enone to afford the corresponding C-apiosides 10 having Î²-configuration.

3'-O-苯甲酰基-2,3-O-异丙叉-D-apio-β-D-呋喃糖基溴 (8)，由 2,3-O-异丙叉-D-apio-β-D- 分两步制备呋喃糖（6）与三（三甲基甲硅烷基）硅烷/AIBN在过量的各种活化烯烃如马来酸二甲酯、丙烯酸甲酯、丙烯腈、甲基乙烯基酮、巴豆醛、环戊-2-烯酮和cyclohex-2-enone 提供相应的 C-apiosides 10 具有 β-构型。