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3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose | 26775-14-4

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

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose

英文别名

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；3-o-Acetyl-1,2:5,6-di-o-isopropylidene-alpha-d-gulofuranose；[(3aR,5S,6R,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] acetate

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose化学式

CAS

26775-14-4

化学式

C₁₄H₂₂O₇

mdl

——

分子量

302.324

InChiKey

QZKDRLZSJSWQPS-IYKVGLELSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

74 °C
沸点：

350.6±42.0 °C(Predicted)
密度：

1.25±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

0.6
重原子数：

21
可旋转键数：

3
环数：

3.0
sp3杂化的碳原子比例：

0.93
拓扑面积：

72.4
氢给体数：

0
氢受体数：

7

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
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-di-O-isopropylidene-D-glucofuranoside	——	C₁₂H₂₀O₆	260.287
——	1,2:5,6-diacetone-D-glucose	582-52-5	C₁₂H₂₀O₆	260.287
——	1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose hydrate	10578-85-5	C₁₂H₂₀O₇	276.287
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
——	1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-ulose	——	C₁₂H₁₈O₆	258.271
——	1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside	3253-75-6	C₁₉H₂₆O₈S	414.477
D-葡萄糖	D-glu	2280-44-6	C₆H₁₂O₆	180.158

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	6-deoxy-3,5-di-O-acetyl-1,2-O-isopropylidene-α-D-allofuranose	110089-59-3	C₁₃H₂₀O₇	288.298
——	6-deoxy-3,5-di-O-acetyl-1,2-O-isopropylidene-α-D-allofuranose	64243-85-2	C₁₃H₂₀O₇	288.298
——	3-O-acetyl-1,2-O-isopropylidene-α-D-allofuranose	51433-05-7	C₁₁H₁₈O₇	262.26
——	3-O-acetyl-5,6-anhydro-1,2-O-isopropylidene-β-L-talofuranose	110089-64-0	C₁₁H₁₆O₆	244.244
——	3-O-acetyl-5,6-anhydro-1,2-O-isopropylidene-α-D-allofuranose	110089-58-2	C₁₁H₁₆O₆	244.244
二丙酮-D-葡萄糖	(1,2:5,6)-di-O-isopropylidene-D-gulose	14686-89-6	C₁₂H₂₀O₆	260.287
——	1,2-O-isopropylidene-6-deoxy-β-L-talofuranose	110089-66-2	C₉H₁₆O₅	204.223
——	6-Desoxy-1,2-O-isopropylidene-α-D-allofuranose	89128-38-1	C₉H₁₆O₅	204.223
——	3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside	4613-62-1	C₁₂H₂₀O₅	244.288
——	3-O-acetyl-6-O-t-butyldimethylsilyl-1,2-O-isopropylidene-α-D-allofuranose	110089-61-7	C₁₇H₃₂O₇Si	376.522
——	(3aR,4R,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-pent-4-enyloxy-tetrahydro-furo[3,4-d][1,3]dioxole	141943-49-9	C₁₇H₂₈O₆	328.406
——	(3aR,4S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-pent-4-enyloxy-tetrahydro-furo[3,4-d][1,3]dioxole	141943-53-5	C₁₇H₂₈O₆	328.406
——	Acetic acid (3aR,5S,6S,6aR)-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester	87256-60-8	C₁₀H₁₅IO₅	342.131
——	(3aR,6S,6aR)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol	34685-42-2	C₁₂H₂₀O₆	260.287
——	(3aR,4R,6S,6aR)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-furo[3,4-d][1,3]dioxol-4-ol	78039-12-0	C₁₂H₂₀O₆	260.287
——	3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranoside	23885-38-3	C₁₉H₂₆O₆	350.412
——	3-O-acetyl-5-deoxy-1,2-O-isopropylidene-5-nitro-α-D-ribofuranose	87256-61-9	C₁₀H₁₅NO₇	261.232
——	1,2:5,6-di-O-isopropylidene-3-deoxy-3-fluoro-α-D-galactofuranose	22435-76-3	C₁₂H₁₉FO₅	262.278
——	Acetic acid (3aR,5R,6R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester	87256-59-5	C₁₇H₂₂O₈S	386.423
——	1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose triflate	74925-16-9	C₁₃H₁₉F₃O₈S	392.35
——	methyl 3-O-benzyl-β-D-gulofuranoside	142929-66-6	C₁₄H₂₀O₆	284.309
——	methyl 3,4-di-O-benzyl-2-O-methyl-β-D-gulopyranoside	142929-67-7	C₂₂H₂₈O₆	388.461
——	(4R,5S,4'R)-2,2,2',2'-Tetramethyl-5-((Z)-pent-2-enyl)-[4,4']bi[[1,3]dioxolanyl]	142034-34-2	C₁₅H₂₆O₄	270.369
——	O6-acetyl-O1,O2-isopropylidene-O5-(toluene-4-sulfonyl)-α-D-glucofuranose	110089-65-1	C₁₈H₂₄O₉S	416.449
——	3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose	19131-08-9	C₁₂H₁₉N₃O₅	285.3
——	(2S,3R,4R,5R,6R)-5,6-dimethoxy-3,4-bis(phenylmethoxy)oxane-2-carbaldehyde	1053613-62-9	C₂₂H₂₆O₆	386.445
——	methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-β-D-gulopyranoside	143058-64-4	C₂₂H₂₆O₆	386.445
——	3-S-Acetyl-1,2:5,6-di-O-isopropylidene-3-thio-α-D-galactofuranose	290362-72-0	C₁₄H₂₂O₆S	318.391
——	Acetic acid (3aR,5S,6R,6aR)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester	110089-63-9	C₂₄H₃₈O₉SSi	530.712
——	methyl 3-O-benzyl-α-D-gulopyranoside	143005-11-2	C₁₄H₂₀O₆	284.309
——	methyl 3-O-benzyl-β-D-gulopyranoside	143005-10-1	C₁₄H₂₀O₆	284.309
——	methyl 3-O-benzyl-4,6-O-benzylidene-β-D-gulopyranoside	143005-12-3	C₂₁H₂₄O₆	372.418
——	3-O-acetyl-6-O-t-butyldimethylsilyl-1,2-O-isopropylidene-5-O-tosyl-α-D-allofuranose	110089-62-8	C₂₄H₃₈O₉SSi	530.712
——	3-Acetamino-3-desoxy-1,2:5,6-di-O-isopropyliden-α-D-galaktofuranose	19131-09-0	C₁₄H₂₃NO₆	301.34
——	(3aR,6S,6aR)-4-Chloro-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole	142034-31-9	C₁₂H₁₉ClO₅	278.733
——	(Z)-(1R,2S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hept-4-ene-1,2-diol	142034-33-1	C₁₂H₂₂O₄	230.304

反应信息

作为反应物：

描述：

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose 在二叔丁基过氧化物、三苯基硅烷作用下，反应 12.0h，以47%的产率得到3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

参考文献：

名称：

A Novel Method for the Deoxygenation of Acetylated Sugars

摘要：

据报道，在均聚条件下，乙酰化的外科胂 1 在三苯基硅烷的作用下转化为脱氧糖 2。带有乙酰化伯醇或仲醇的呋喃糖和吡喃糖都能有效地脱氧。

DOI：

10.1055/s-1988-27593
作为产物：

描述：

双丙酮葡萄糖在吡啶、甲醇、三乙基硅烷、 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物、 palladium 10% on activated carbon 、水、 sodium acetate 、 sodium bromide 作用下，以乙酸乙酯为溶剂，反应 24.5h，生成 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose

参考文献：

名称：

[EN] LARGE SCALE PROCESS FOR PREPARING 1,2,4, 6-TETRA-0-ACETYL-3-AZID0-3-DE0XY-D-GALACT0PYRAN0SIDE
[FR] PROCÉDÉ À GRANDE ÉCHELLE POUR LA PRÉPARATION DE 1,2,4,6-TÉTRA-O-ACÉTYL-3-AZIDO-3-DÉSOXY-D-GALACTOPYRANOL

摘要：

本发明涉及一种制备化合物(X)的方法，该方法适用于大规模合成。

公开号：

WO2021198160A1

点击查看最新优质反应信息

文献信息

Synthesis of a MUC1-glycopeptide–BSA conjugate vaccine bearing the 3′-deoxy-3′-fluoro-Thomsen–Friedenreich antigen

作者：Anja Hoffmann-Röder、Manuel Johannes

DOI：10.1039/c1cc13184b

日期：——

A novel MUC1-glycopeptideâBSA conjugate vaccine with a specifically fluorinated ThomsenâFriedenreich antigen side chain at Thr6 was prepared. Preliminary immunological experiments reveal specific binding of the tumor-associated glycopeptide antigen analog by anti-MUC1-mouse antibodies.

一种新型的MUC1糖肽–BSA conjugate疫苗被制备，其中在Thr6位点具有特别氟化的Thomsen–Friedenreich抗原侧链。初步免疫学实验显示抗MUC1小鼠抗体对肿瘤相关糖肽抗原类似物的特异性结合。
Improved double epimerisation of (D)-glucose into (D)-gulose and the synthesis of (D)-xylo-imidazolopiperidinose

作者：Hervé Siendt、Théophile Tschamber、Jacques Streith

DOI：10.1016/s0040-4039(99)01003-5

日期：1999.7

Rhodium/alumina catalysed cis-hydrogenation of the known enol-acetate 7 proceeded quantitatively and with complete stereoselectivity leading to the D-gulose derivative 8. Several reaction steps permitted transformation of 8 into the target D-xylo-imidazolopiperidinose ent-4 molecule, i.e. the enantiomer of the already known imidazolo-sugar 4.

铑/氧化铝催化的已知烯醇-乙酸酯7的顺式氢化反应是定量进行的，并且具有完全的立体选择性，从而生成D-古洛糖衍生物8。几个反应步骤允许将8转化为目标D-木糖-咪唑并哌啶子糖ent - 4分子，即已知咪唑糖4的对映异构体。
Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses

作者：Tomáš Malatinský、Mária Spišáková、Matej Babjak、Jana Doháňošová、Jaromír Marek、Ján Moncol、Róbert Fischer

DOI：10.1002/ejoc.201601488

日期：2017.2.10

Two five-membered cyclic nitrones derived from hexoses, a newly synthesized D-allo-configured nitrone and an already known D-talo-configured nitrone, have been examined in 1,3-dipolar cycloaddition reactions with vinyl acetate, allyl benzoate, methyl acrylate, acrylonitrile, and vinylene carbonate. The reactions of the D-allo-configured nitrone proceeded preferentially through the expected exo-anti

已在与乙酸乙烯酯、苯甲酸烯丙酯、丙烯酸甲酯的 1,3-偶极环加成反应中研究了两种衍生自己糖的五元环硝酮、一种新合成的 D-allo-构型硝酮和一种已知的 D-talo-构型硝酮、丙烯腈和碳酸亚乙烯酯。D-allo-配置的硝酮的反应优先通过预期的外-反过渡态进行，但 D-talo-配置的硝酮的所有环加成令人惊讶地显示出高外-syn 选择性。这种立体选择性的逆转可以通过从 X 射线数据中获得的硝酮优选构象的 3D 分析来解释。使用 CONFLEX、PM5 和 DFT 计算进一步检查结构。
Synthesis of 5-amino-5-deoxy-d-galactopyranose and 1,5-dideoxy-1,5-imino-d-galactitol, and their inhibition of α- and β-d-galactosidases

作者：Günter Legler、Stefan Pohl

DOI：10.1016/s0008-6215(00)90138-1

日期：1986.11

chlorobenzene. α- d -Galactosidase from coffee beans and from Escherichia coli and β- d -galactosidase from E. coli and Aspergillus wentii were inhibited with K i values that ranged from 0.0007 to 8.0μ m . Formation of the enzyme-inhibitor complexes with the d -galactose analogue was on the time-scale of minutes, whereas the d -galactitol analogue showed a slow approach to the inhibition only with α- d -galactosidase

摘要提出了从1,2：5,6-二-O-异亚丙基-α-d-葡萄糖呋喃糖开始的十二步合成方法，用于制备标题化合物及其左旋类似物。它们的合成是基于用阮内镍还原1-阿拉伯糖基己糖呋喃糖-5-ulose的受保护的5-羟基亚氨基衍生物，以及制备ad-半乳糖呋喃糖衍生物的以下改进：在C-3上用重铬酸吡啶鎓氧化-乙酸酐，将3-O-乙酰基-己-3--3-呋喃呋喃糖中间体立体定向还原为d-古洛衍生物，并用乙酸四丁铵在氯苯中的C-3转化其3-甲苯磺酸酯。来自咖啡豆和大肠杆菌的α-d-半乳糖苷酶以及来自大肠杆菌和戈氏曲霉的β-d-半乳糖苷酶的K i值在0.0007至8.0μm范围内。与d-半乳糖类似物形成酶抑制剂复合物的时间为数分钟，而d-半乳糖醇类似物显示出仅用咖啡豆中的α-d-半乳糖苷酶和β-d-抑制作用的缓慢方法。半乳曲霉的半乳糖苷酶。d-半乳糖醇类似物的N-烷基化对抑制是有害的，除了来自大肠杆菌的β-d-半
Synthesis of Uridine 5′‐[2‐<i>S</i>‐Pyridyl‐3‐thio‐α‐<scp>d</scp>‐galactopyranosyl Diphosphate]: Precursors of UDP‐Thiogal Sugar Nucleotide Donor Substrate for β‐1,4‐Galactosyltransferase

作者：Jordan Elhalabi、Kevin G. Rice

DOI：10.1081/ncn-120027828

日期：2004.1.1

The syntheses of a novel uridine diphosphate galactose (UDP‐Gal) analog, (UDP‐2,4,6‐tri‐O‐acetyl‐3‐S‐acetyl‐3‐thio‐α‐d‐galactopyranose) (11) and the thiolpyridine protected (Uridine 5′‐[3‐S‐(2‐S‐pyridyl)‐3‐thio‐α‐d‐galactopyranosyl diphosphate) analog (12) are described. The reported synthesis relies on the novel use of thiolpyridine to generate 12 which is a suitably protected intermediate for generating

新型尿苷二磷酸半乳糖 (UDP-Gal) 类似物的合成 (UDP-2,4,6-tri-O-acetyl-3-S-acetyl-3-thio-α-d-galactopyranose) (11) 和描述了硫醇吡啶保护的（尿苷 5'-[3-S-（2-S-吡啶基）-3-硫代-α-d-吡喃半乳糖基二磷酸）类似物（12）。报道的合成依赖于硫醇吡啶的新用途来生成 12，它是一种适当保护的中间体，用于在通过 β-1,4-半乳糖基转移酶进行酶转移之前通过还原生成 UDP-thioGal 衍生物。†为了纪念和庆祝 Leroy B. Townsend 教授 70 岁生日。