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6-脱氧-6-碘-1,2:3,4-二-o-异亚丙基-α-d-半乳糖吡喃糖苷 | 4026-28-2

分子结构分类

有机化合物 - 有机杂环化合物 - 二氧吡喃

中文名称

6-脱氧-6-碘-1,2:3,4-二-o-异亚丙基-α-d-半乳糖吡喃糖苷

中文别名

6-脱氧-1,2:3,4-二-O-异亚丙基-6-碘-ALPHA-D-吡喃半乳糖；6-碘-1,2:3,4-双-O-异丙亚基-Α-D-吡喃半乳糖

英文名称

1,2:3,4-di-O-isopropylidene-6-iodo-D-galactopyranose

英文别名

6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose；6-iodo-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose；(1S,2R,6R,8S,9R)-8-(iodomethyl)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane

6-脱氧-6-碘-1,2:3,4-二-o-异亚丙基-α-d-半乳糖吡喃糖苷化学式

CAS

4026-28-2

化学式

C₁₂H₁₉IO₅

mdl

——

分子量

370.184

InChiKey

JMIGDGVTFPSEMQ-SOYHJAILSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

70-71℃

计算性质

辛醇/水分配系数(LogP)：

1.8
重原子数：

18
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：293789ff758a8b2ca68f7cb17f51292b

查看

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
双丙酮半乳糖	1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	4064-06-6	C₁₂H₂₀O₆	260.287
——	1,2:3,4-di-O-isopropylidene-6-O-methylsulphonyl-α-D-galactopyranose	4148-55-4	C₁₃H₂₂O₈S	338.379
——	1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose	71001-09-7	C₁₃H₁₉F₃O₈S	392.35
1,2:3,4-二-o-异亚丙基-6-o-对甲苯磺酰基-alpha-D-半乳糖	(1,2:3,4-di-O-isopropylidene-6-O-(p-toluensulfonate))-D-galactopiranose	4478-43-7	C₁₉H₂₆O₈S	414.477
——	1,2:3,4-di-O-isopropylidene-6-O-(N-imidazole-1-sulfonyl)-α-D-galactopyranose	80667-80-7	C₁₅H₂₂N₂O₈S	390.414
alpha-D-半乳糖	α-D-galactopyranose	3646-73-9	C₆H₁₂O₆	180.158
D-吡喃葡萄糖	D-Galactose	10257-28-0	C₆H₁₂O₆	180.158

下游产品

中文名称	英文名称	CAS号	化学式	分子量
1,2,3,4-二-O-异亚丙基-alpha-D-岩藻吡喃糖	1,2:3,4-di-O-isopropylidene-α-D-fucopyranose	4026-27-1	C₁₂H₂₀O₅	244.288
双丙酮半乳糖	1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	4064-06-6	C₁₂H₂₀O₆	260.287
——	6,6'-bis(1,2:3,4-di-O-isopropylidene-6-deoxy-α-D-galactopyranose)	61252-75-3	C₂₄H₃₈O₁₀	486.56
——	(-)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-heptopyranose	52562-76-2	C₁₃H₂₂O₆	274.314
——	1,2:3,4-di-O-isopropylidene-α-D-galacto-non-8-enopyranose	155480-30-1	C₁₅H₂₄O₅	284.353
——	(-)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-heptodialdo-1,5-pyranose	75251-47-7	C₁₃H₂₀O₆	272.298
——	(-)-6-cyano-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	56760-91-9	C₁₃H₁₉NO₅	269.298
——	6-amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	4711-01-7	C₁₂H₂₁NO₅	259.302
——	6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-D-galctopyranose	——	C₁₂H₁₉FO₅	262.278
1,2：3,4-二-O-异亚丙基-α-D-半乳糖-己二醛-1,5-吡喃糖	(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde	4933-77-1	C₁₂H₁₈O₆	258.271
——	3-deoxy-3-C-<(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose	79101-57-8	C₂₅H₄₀O₁₀	500.587
1,2:3,4-二-o-异亚丙基-6-硫代-a-d-吡喃葡萄糖	1,2:3,4-di-O-isopropylidene-6-thio-α-D-galactopyranose	16714-07-1	C₁₂H₂₀O₅S	276.354
——	ethyl (E)-(6,7,8-trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-non-7-enopyranosid)uronate	160452-99-3	C₁₇H₂₆O₇	342.389
——	6-(2-hydroxyethylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	950845-61-1	C₁₄H₂₅NO₆	303.356
——	6-(3-aminopropylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	950845-58-6	C₁₅H₂₈N₂O₅	316.398
——	6-[(2-hydroxydodecyl)amino]-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	——	C₂₄H₄₅NO₆	443.624
——	6-(2-aminoethylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	125008-73-3	C₁₄H₂₆N₂O₅	302.371
——	6-S-allyl-1,2:3,4-di-O-isopropylidene-6-thio-α-D-galactopyranose	——	C₁₅H₂₄O₅S	316.419
——	6-[N-octyl-N-(2-hydroxyethyl)amino]-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	——	C₂₂H₄₁NO₆	415.571
——	6-S-acetyl-6-deoxy-1,2:3,4-di-O-isopropylidene-6-thio-α-D-galactopyranose	16714-06-0	C₁₄H₂₂O₆S	318.391
——	1,2,3,4-tetra-O-acetyl-β-D-fucopyranose	34371-41-0	C₁₄H₂₀O₉	332.307
——	5,6-Dideoxy-1,2:3,4-di-O-isopropylidene-L-arabino-5-hexenose	351345-12-5	C₁₂H₂₀O₅	244.288
——	5-[6'-deoxy-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)]tetrazole	313355-82-7	C₁₃H₂₀N₄O₅	312.326
——	6-deoxy-6-phenyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose	——	C₁₈H₂₄O₅	320.386
——	6-deoxy-1,2,3,4-di-O-isopropylidene-L-arabino-hex-5-enopyranoside	22618-03-7	C₁₂H₁₈O₅	242.272
——	(Z)-1-(benzyl 2,3-O-isopropylidene-β-D-ribo-tetrafuranosid-4-yl)-2-(1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranos-5-yl)ethylene	——	C₂₇H₃₆O₉	504.577
——	2-Methyl-acrylic acid 2,2,6,6-tetramethyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-piperidin-4-yl ester	869812-08-8	C₂₅H₄₁NO₈	483.602
——	2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranose	156719-47-0	C₂₇H₃₀O₅	434.532
——	2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranose	——	C₂₇H₃₀O₅	434.532
——	4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-piperidine	869812-06-6	C₂₇H₅₁NO₇Si	529.79
——	(2,3,4,5,6-pentafluorophenyl) 3-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]propane-1-sulfonate	452905-66-7	C₂₀H₂₃F₅O₈S	518.456

反应信息

作为反应物：

描述：

6-脱氧-6-碘-1,2:3,4-二-o-异亚丙基-α-d-半乳糖吡喃糖苷在溶剂黄146 、锌作用下，以苯为溶剂，反应 16.0h，生成双丙酮半乳糖

参考文献：

名称：

氧化还原糖苷化：在高立体选择性蔗糖合成中使用Nozaki-Takai亚甲基化

摘要：

2,3,4,6-四-O-苄基-D-吡喃葡萄糖（7）与丁基锂和2- [2,3,5-三-O-苄基-4-O-（叔丁基二苯基甲硅烷基）的顺序反应-D-阿拉伯糖酰基]硫代-3-硝基吡啶（6）在-78度下得到2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基2,3,5-三-O-苄基-4 -O-（叔丁基二苯基甲硅烷基）-D-阿拉伯糖+（8; 71％，α：β大于50：1）。在二氧化硅存在下进行酯羰基亚甲基化，甲硅烷基化和碘醚化，得到3,4,6-三-O-苄基-1-脱氧-1-碘-（2,3,4,6-四-O-苄基-α -D-吡喃葡萄糖基）-β-D-果糖呋喃糖苷（15; 44％，α：beta大于50：1）。通过使用TEMPO（24）进行自由基取代，然后将钠氨还原，乙酰化和Zemplen甲醇分解，将该新戊碘化物15转化为蔗糖（1; 80％）。

DOI：

10.1016/0008-6215(92)80059-a
作为产物：

描述：

双丙酮半乳糖在咪唑、碘、三苯基膦作用下，以甲苯为溶剂，以90%的产率得到6-脱氧-6-碘-1,2:3,4-二-o-异亚丙基-α-d-半乳糖吡喃糖苷

参考文献：

名称：

烷基化氨基醇及其糖基化衍生物的制备及其抗结核活性。

摘要：

合成了一系列的N-和C-烷基化的氨基醇及其受保护的吡喃半乳糖基衍生物，并评估了其抗结核活性。这些化合物中的五种显示出良好的活性，MIC低于12.5mug / mL。碳水化合物的存在对抗菌活性有轻微的影响。

DOI：

10.1016/j.bmc.2007.08.045

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文献信息

Preparation of glycosyl disulfides and sulfides via the formation of glycosyl Bunte salts as thiol surrogates

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DOI：10.1016/j.tet.2021.132242

日期：2021.5

odourless reaction condition has been developed for the preparation of symmetrical glycosyl disulfide derivatives and aryl glycosyl disulfide derivatives from corresponding glycosyl iodides via formation of glycosyl Bunte salts as thiol surrogates. The reaction has been further extended towards the preparation of glycosyl sulfides derivatives from corresponding Bunte salt in the presence of sodium sulphide

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A New Route to Sulfonamides via Intermolecular Radical Addition to Pentafluorophenyl Vinylsulfonate and Subsequent Aminolysis

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DOI：10.1021/ol026181m

日期：2002.7.1

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[反应：见正文]由相应的碘或溴化合物和氢化三正丁基锡生成的各种自由基以分子间方式添加到活化的受体五氟苯基乙烯基磺酸盐中。然后，将每个反应的产物用多种不同的胺进行氨解。
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作者：Siling Zhao、Neal P. Mankad

DOI：10.1002/anie.201801814

日期：2018.5.14

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日期：2019.6.21

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Total synthesis of puberulic acid has been achieved via 8 steps, with 54% yield, using d-(+)-galactose as a framework source.

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