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3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside | 4613-62-1

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-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

英文别名

3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose；3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；(3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole；1,2:5,6-di-O-isopropylidene-3-deoxy-α-D-ribo-hexofuranose；(3aR,5S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside化学式

CAS

4613-62-1

化学式

C₁₂H₂₀O₅

mdl

——

分子量

244.288

InChiKey

AKKRBVFGAWFTRW-SGIHWFKDSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

105-115 °C(Press: 3 Torr)
密度：

1.123±0.06 g/cm3(Predicted)
溶解度：

溶于氯仿、乙酸乙酯

计算性质

辛醇/水分配系数(LogP)：

1
重原子数：

17
可旋转键数：

1
环数：

3.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

46.2
氢给体数：

0
氢受体数：

5

SDS

SDS：b33d6d2eb96a0e7911ba1980a2d21428

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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
——	1,2:5,6-di-O-isopropylidene-3-deoxy-α-D-ribo-hexofuranose	81097-00-9	C₁₂H₂₀O₅	244.288
——	1,2:5,6-di-O-isopropylidene-α-D-glucofuranose	350255-13-9	C₁₂H₂₀O₆	260.287
双丙酮葡萄糖	1,2:5,6-di-O-isopropylidene-α-D-glucofuranose	582-52-5	C₁₂H₂₀O₆	260.287
二丙酮-D-葡萄糖	(1,2:5,6)-di-O-isopropylidene-D-gulose	14686-89-6	C₁₂H₂₀O₆	260.287
——	1,2:5,6-diacetone-D-glucose	582-52-5	C₁₂H₂₀O₆	260.287
3-O-乙酰基-1,2:5,6-二-O-异丙基-Alpha-D-呋喃(型)葡萄糖	3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose	16713-80-7	C₁₄H₂₂O₇	302.324
3-O-苄基-1,2:5,6-O-双异丙叉-α-D-呋喃葡萄糖	3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose	18685-18-2	C₁₉H₂₆O₆	350.412
——	1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate)	16667-96-2	C₁₄H₂₂O₆S₂	350.457
——	1,2:5,6-di-O-isopropylidene-3-O-<(methylthio)thiocarbonyl>-α-D-glucofuranose	——	C₁₄H₂₂O₆S₂	350.457
——	1,2:5,6-di-O-isopropylidene-3-O-trifluoroacetyl-α-D-glucofuranose	76719-48-7	C₁₄H₁₉F₃O₇	356.296
——	3-bromo-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose	74958-56-8	C₁₂H₁₉BrO₅	323.184
——	1,2:5,6-di-O-isopropylidene-3-O-[(trideuteromethylthio)thiocarbonyl]-α-D-gucofuranose	——	C₁₄H₂₂O₆S₂	353.433
——	O-((3aR,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl) O-phenylcarbonothioate	19189-62-9	C₁₉H₂₄O₇S	396.461
——	1,2:5,6-di-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose	——	C₂₀H₂₈O₇	380.438
——	O-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]] N,N-diethylcarbamothioate	31818-51-6	C₁₇H₂₉NO₆S	375.486
——	1,2:5,6-di-O-isopropylidene-3-O-(4-fluorophenoxy)thionocarbonyl-α-D-glucofuranose	130534-83-7	C₁₉H₂₃FO₇S	414.452
——	1,2:5,6-di-O-isopropylidene-3-(N-phenylthioxocarbamoyl)-α-D-glucofuranose	165589-85-5	C₁₉H₂₅NO₆S	395.477
——	3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose	13964-22-2	C₁₉H₂₄O₇	364.395
——	1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose	55951-93-4	C₁₃H₁₉F₃O₈S	392.35
——	1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose	55951-90-1	C₁₃H₁₉F₃O₈S	392.35
——	O-[1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl] 1H-imidazole-1-carbothioate	79233-85-5	C₁₆H₂₂N₂O₆S	370.426
——	bis(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl) diselenide	1221269-55-1	C₂₄H₃₈O₁₀Se₂	644.48
——	3-S-Acetyl-1,2:5,6-di-O-isopropylidene-3-thioalphad-allofuranose	——	C₁₄H₂₂O₆S	318.39
——	1,2:5,6-Di-O-isopropylidene-3-O-<(pentafluorophenoxy)thiocarbonyl>-α-D-glucofuranose	124344-20-3	C₁₉H₁₉F₅O₇S	486.414
——	1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside	3253-75-6	C₁₉H₂₆O₈S	414.477

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	1,2:5,6-di-O-isopropylidene-3-deoxy-α-D-ribo-hexofuranose	81097-00-9	C₁₂H₂₀O₅	244.288
——	3-deoxy-1,2-O-isopropylidene-D-glucose	——	C₉H₁₆O₅	204.223
——	(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol	327594-26-3	C₉H₁₆O₅	204.223
1,2:5,6-二异亚丙基-alpha-D-异呋喃糖	Diacetone D-glucose	2595-05-3	C₁₂H₂₀O₆	260.287
——	1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofurano[2,3-d][1,3]dioxol-5-yl]ethanol	221372-79-8	C₉H₁₆O₄	188.224
——	3,6-dideoxy-α-D-glucofuranose	58475-17-5	C₉H₁₆O₄	188.224
——	(3aR,5S,6aR)-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole	2457-93-4	C₉H₁₄O₄	186.208
5,6-脱水-3-脱氧-1,2-O-(1-甲基亚乙基)-beta-L-呋喃来苏己糖	5,6-anhydro-3-deoxy-1,2-O-isopropylidene-β-L-lyxo-hexofuranose	20720-51-8	C₉H₁₄O₄	186.208
——	3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose	3396-71-2	C₈H₁₄O₄	174.197
——	(3aR,5R,6aR)-2,2-dimethyl-5-propyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole	721923-19-9	C₁₀H₁₈O₃	186.251
——	5,6-di-O-benzyl-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranoside	112031-55-7	C₂₃H₂₈O₅	384.472
——	(3aR,5S,6aR)-2,2-dimethyl-5-[(1R)-1-phenylmethoxyethyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole	169392-04-5	C₁₆H₂₂O₄	278.348
——	6-azido-3,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose	284031-17-0	C₉H₁₅N₃O₄	229.236
——	6-O-(tert-butyldimethylsilyl)-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranose	124666-60-0	C₁₅H₃₀O₅Si	318.486
1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖	1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose	2847-00-9	C₁₂H₁₈O₆	258.271
——	3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-hex-5-enofuranoside	96852-88-9	C₉H₁₄O₃	170.208
——	O¹,O²-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose	——	C₈H₁₂O₄	172.181
——	5-O-benzyl-3-deoxy-1,2-O-isopropylidee-α-D-ribofuranose	116306-89-9	C₁₅H₂₀O₄	264.321
——	3-deoxy-1,2-isopropylidene-α-D-ribofuronic acid	163042-94-2	C₈H₁₂O₅	188.18
——	(3aR,5S,6aR)-2,2-dimethyl-5-[(Z)-prop-1-enyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole	721923-18-8	C₁₀H₁₆O₃	184.235
——	methyl (3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate	126694-09-5	C₉H₁₄O₅	202.207
1,2,4,6-O-四乙酰基-3-脱氧-D-吡喃葡萄糖	1,2,4,6-tetra-O-acetyl-3-deoxy-D-glucopyranose	5040-09-5	C₁₄H₂₀O₉	332.307
——	3,6,7-trideoxy-1,2-O-isopropylidene-7-C-methylene-β-L-lyxo-octofuranurono-8,5-lactone	——	C₁₂H₁₆O₅	240.256
——	3,6,7-trideoxy-1,2-O-isopropylidene-7-C-methylene-α-D-ribo-octofuranurono-8,5-lactone	——	C₁₂H₁₆O₅	240.256
——	1,2-O-isopropylidene-3-deoxy-5,6-di-O-methylsulphonyl-α-D-glucofuranose	96852-87-8	C₁₁H₂₀O₉S₂	360.406
——	[(3aR,5S,6aR)-2,2-dimethyltetrhydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate	4105-29-7	C₁₅H₁₈O₅	278.305
——	3-deoxy-α-D-ribo-hexofuranose	75800-78-1	C₆H₁₂O₅	164.158
——	N-benzyl-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanamine	1365659-10-4	C₁₅H₂₁NO₃	263.337
——	1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-N-benzylmethanimine	1255906-08-1	C₁₅H₁₉NO₃	261.321
——	6-O-(tert-butyldimethylsilyl)-3-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose	124666-61-1	C₁₅H₂₈O₅Si	316.47
——	3-deoxy-5-O-methylsulfonyl-4-[(methylsulfonyloxy)methyl]-1,2-O-isopropylidene-α-D-glycero-pentofuranose	474926-90-4	C₁₁H₂₀O₉S₂	360.406
——	3-deoxy-D-ribo-hexopyranose	36204-29-2	C₆H₁₂O₅	164.158
——	3-deoxy-β-D-glucose	75800-77-0	C₆H₁₂O₅	164.158
——	3-deoxy-α-D-ribo-hexopyranose	75800-76-9	C₆H₁₂O₅	164.158

反应信息

作为反应物：

描述：

3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在硫酸作用下，生成 3-脱氧-d-葡萄糖

参考文献：

名称：

Cerny; Pacak, Collection of Czechoslovak Chemical Communications, 1956, vol. 21, p. 1003,1005

摘要：

DOI：
作为产物：

描述：

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在咪唑、偶氮二异丁腈、三正丁基氢锡、 sodium hydride 作用下，以四氢呋喃、甲苯为溶剂，反应 6.75h，生成 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

参考文献：

名称：

从 D-葡萄糖合成 (2S,4S)-4-羟脯氨酸

摘要：

由于 N-苄基-和 Z-保护基团的脱保护以及 C-2-O-甲磺酸酯在一锅反应中被 C-5 胺分子内亲核取代。胺 11 的 Z-保护，然后酸催化水解得到缩醛 13。使用 NaBH4 还原缩醛得到 Z-脯氨醇 14。二醇 14 被 (2,2,6,6-四甲基哌啶-1-基)-氧基(TEMPO)/[(双)(乙酰氧基)碘]苯(BAIB)和NaClO2/NaH2PO4，然后Z-脱保护，从D-葡萄糖以3.5%的总产率得到标题化合物I。图形概要然后Z-脱保护，从D-葡萄糖以3.5%的总产率得到标题化合物I。图形概要然后Z-脱保护，从D-葡萄糖以3.5%的总产率得到标题化合物I。图形概要

DOI：

10.1080/00397911.2010.539753

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文献信息

Facile Barton−McCombie Deoxygenation of Alcohols with Tetrabutylammonium Peroxydisulfate and Formate Ion

作者：Hee Sock Park、Hee Yoon Lee、Yong Hae Kim

DOI：10.1021/ol050886h

日期：2005.7.1

[reaction: see text]. A new method for efficient radical deoxygenation of alcohols is described for preparing bulk chemicals avoiding scale-up problems. Treatment of various thiocarbonyl derivatives with (Bu(4)N)(2)S(2)O(8) and HCO(2)Na in DMF afforded the corresponding deoxygenated products in excellent yields. The deoxygenation appears to be initiated by the transfer of a single electron to thiocarbonyl

[反应：请参见文字]。描述了一种用于醇的有效自由基脱氧的新方法，用于制备散装化学品以避免规模扩大的问题。用（Bu（4）N）（2）S（2）O（8）和HCO（2）Na在DMF中处理各种硫代羰基衍生物以优异的收率提供了相应的脱氧产物。脱氧似乎是由单个电子从CO（2）（*）（-）而不是SO4（*）（-）转移到硫代羰基衍生物而引发的。
Boryltrihydroborate: Synthesis, Structure, and Reactivity as a Reductant in Ionic, Organometallic, and Radical Reactions

作者：Kyoko Nozaki、Yoshitaka Aramaki、Makoto Yamashita、Shau-Hua Ueng、Max Malacria、Emmanuel Lacôte、Dennis P. Curran

DOI：10.1021/ja105277u

日期：2010.8.25

dimer lacks the bridging B-H bonds seen in neutral boranes and is instead held together by ionic Li---HB interactions. A preliminary scan of reactions with several iodides shows that the compound participates in an ionic reduction (with a primary-alkyl iodide), an organometallic reduction (Pd-catalyzed with an aryl iodide), and a radical reduction (AIBN-initiated with a sugar-derived iodide). Accordingly

锂 1,3-双(2,6-二异丙基苯基)-2,3-二氢-1H-1,3,2-二氮杂硼醇-2-ide 与硼烷反应。THF 提供了第一个硼基取代的硼氢化物：锂 [1 ,3-双(2,6-二异丙基苯基)-2,3-二氢-1H-1,3,2-二氮杂硼醇-2-基]三氢硼酸盐。该化合物通过 (11)B、(1)H 和 (7)Li NMR 光谱和其他方法进行了充分表征，并将这些数据与中性和阴离子基准化合物进行了比较。该化合物结晶为与四个 THF 分子复合的二聚体。二聚体缺乏在中性硼烷中看到的桥接 BH 键，而是通过离子 Li---HB 相互作用结合在一起。对几种碘化物反应的初步扫描表明，该化合物参与了离子还原（用伯烷基碘）、有机金属还原（用芳基碘催化的钯）、和自由基还原（AIBN 由糖衍生的碘化物引发）。因此，新的硼基硼氢化物类可能具有传统硼氢化物和等电子 N-杂环卡宾硼烷的特性。
Radical Deoxygenation of Xanthates and Related Functional Groups with New Minimalist N-Heterocyclic Carbene Boranes

作者：Shau-Hua Ueng、Louis Fensterbank、Emmanuel Lacôte、Max Malacria、Dennis P. Curran

DOI：10.1021/ol101015m

日期：2010.7.2

Minimalist N-heterocyclic carbene boranes 1,3-dimethylimidazol-2-ylideneborane and 2,4-dimethyl-1,2,4-triazol-3-ylideneborane are readily available and have low molecular weights. They exhibit superior performance to first-generation NHC−boranes, providing improved yields in reductions of xanthates and related functional groups.

极简主义的N-杂环卡宾硼烷1,3-二甲基咪唑-2-亚基硼烷和2,4-二甲基-1,2,4-三唑-3-亚基硼烷很容易获得，并且分子量低。它们表现出优于第一代NHC-硼烷的性能，在减少黄药和相关官能团方面提供了更高的收率。
The invention of radical reactions. Part XXXI. Diphenylsilane: a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry

作者：Derek H.R. Barton、Doo Ok Jang、Joseph Cs. Jaszberenyi

DOI：10.1016/s0040-4020(01)87198-2

日期：1993.8

Various thionocarbonates and xanthates of alcohols and bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins, while bromides and iodides are dehalogenated with diphenylphenylsilane in good yield.

各种thionocarbonates和醇的黄原酸盐和二的-xanthates VIC -diols容易脱氧成相应的烃或烯烃，而溴化物和碘化物与以良好的收率diphenylphenylsilane脱卤。
Polarity Reversal Catalysis in Radical Reductions of Halides by N-Heterocyclic Carbene Boranes

作者：Xiangcheng Pan、Emmanuel Lacôte、Jacques Lalevée、Dennis P. Curran

DOI：10.1021/ja300416f

日期：2012.3.28

ineffective radical reductions of alkyl and aryl halides by N-heterocyclic carbene boranes (NHC-boranes) are catalyzed by thiols. Reductions and reductive cyclizations with readily available 1,3-dimethylimidazol-2-ylidene borane and a water-soluble triazole relative are catalyzed by thiophenol and tert-dodecanethiol [C(9)H(19)C(CH(3))(2)SH]. Rate constants for reaction of the phenylthiyl (PhS•) radical with

否则，N-杂环卡宾硼烷（NHC-硼烷）对烷基和芳基卤化物的缓慢或完全无效的自由基还原由硫醇催化。使用容易获得的 1,3-二甲基咪唑-2-亚基硼烷和水溶性三唑相关物的还原和还原环化反应由苯硫酚和叔十二烷硫醇催化 [C(9)H(19)C(CH(3))(2 )SH]。苯硫基 (PhS•) 自由基与两个 NHC 硼烷反应的速率常数已通过激光闪光光解实验测量为 ~10(8) M(-1) s(-1)。对现有证据的分析表明极性反转催化的作用。