ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate | 108788-49-4

分子结构分类

有机化合物 - 苯类化合物 - 苯和取代衍生物

中文名称

——

中文别名

——

英文名称

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

英文别名

(E)-ethyl-(3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene)-α-D-1,4-heptofuranosyl-5-enoate；(E)-ethyl-1,2-O-isopropylidene-3-O-benzyl-5,6-dideoxy-α-D-xylo-5-eno-heptofuranuronate；ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5(E)-eno-heptofuranuronoate；ethyl (5E)-3-O-Benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranuroate；ethyl (E)-3-O-benzyl-1,2-O-isopropylidene-5,6-dideoxy-α-D-xylo-5-enoheptofuranuronate；ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate；ethyl (E)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enoate

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate化学式

CAS

108788-49-4

化学式

C₁₉H₂₄O₆

mdl

——

分子量

348.396

InChiKey

QKUAHWSYIPGNSW-BKXKVBGLSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

2.2
重原子数：

25
可旋转键数：

7
环数：

3.0
sp3杂化的碳原子比例：

0.53
拓扑面积：

63.2
氢给体数：

0
氢受体数：

6

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
3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖	3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose	23558-05-6	C₁₅H₁₈O₅	278.305

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose	108182-63-4	C₁₇H₂₂O₅	306.359
——	(E)-3-((2R,3R,4R,5S)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester	247144-48-5	C₁₆H₂₀O₆	308.331
——	3-O-benzyl-1,2-O-isopropylidene-5,6-dideoxy-α-D-xylo-heptofuranose	72277-36-2	C₁₇H₂₄O₅	308.375
——	3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-α-D-glycero-L-ido-hepto-1,4-furanose	108788-47-2	C₁₇H₂₂O₆	322.358
——	3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-β-L-glycero-D-gluco-hepto-1,4-furanose	108788-46-1	C₁₇H₂₂O₆	322.358
——	ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate	729596-15-0	C₁₉H₂₆O₈	382.411
——	ethyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-L-ido-heptofuranuronate	729596-16-1	C₁₉H₂₆O₈	382.411
——	6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose	108788-52-9	C₁₇H₂₃N₃O₆	365.386
——	6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-L-glycero-L-ido-heptofuranose	108788-53-0	C₁₇H₂₃N₃O₆	365.386
——	3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose	1289557-58-9	C₁₈H₂₁NO₄S	347.435
——	ethyl [5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate	742077-97-0	C₁₉H₂₇NO₆	365.426
——	ethyl 5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-1,4-heptofuranuronate	498575-43-2	C₁₉H₂₇NO₆	365.426
——	5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose	108788-60-9	C₁₇H₂₁N₃O₅	347.371
——	5,7-anhydro-6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-L-glycero-L-ido-heptofuranose	108788-61-0	C₁₇H₂₁N₃O₅	347.371
——	3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose	1289557-66-9	C₁₉H₂₅NO₆	363.411
——	ethyl 1,2-O-isopropylidene-3-O-benzyl-5-nitromethyl-5,8-dideoxy-β-L-ido-heptofuranuronate	1071912-14-5	C₂₀H₂₇NO₈	409.436
——	(1R,2R,3S,4R,5R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-α-D-gluco-heptofuranuronate	517877-04-2	C₂₃H₃₅NO₆	421.534
——	ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-butylamino)-5,6-dideoxy-β-L-ido-heptofuranuronate	623559-41-1	C₂₃H₃₅NO₆	421.534
——	ethyl 3-O-benzyl-5-(benzylamino)-5,6-dideoxy-1,2-O-isopropylidene-heptofuranuronate	——	C₂₆H₃₃NO₆	455.551
——	(4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester	729596-17-2	C₁₉H₂₄O₁₀S	444.46
——	(4S,5R)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester	729596-21-8	C₁₉H₂₄O₁₀S	444.46
——	methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate	1289557-72-7	C₁₉H₂₅NO₈	395.409
——	6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-glycero-D-gluco-heptofuranose	108788-56-3	C₂₄H₂₉N₃O₈S	519.576
——	6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-L-glycero-L-ido-heptofuranose	108788-57-4	C₂₄H₂₉N₃O₈S	519.576
——	6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-β-L-glycero-L-ido-heptofuranose	729596-23-0	C₁₈H₂₅NO₈	383.398
——	6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose	729596-19-4	C₁₈H₂₅NO₈	383.398
——	5,7-anhydro-6-N-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-L-glycero-L-ido-heptofuranose	108788-65-4	C₁₈H₂₃NO₇	365.383
——	5,7-anhydro-6-N-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose	108788-64-3	C₁₈H₂₃NO₇	365.383

反应信息

作为反应物：

描述：

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate 在二异丁基氢化铝作用下，以四氢呋喃为溶剂，反应 2.0h，以93%的产率得到3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose

参考文献：

名称：

Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide

摘要：

The Sharp less asymmetric epoxidation of D-glucose-derived ally! alcohol 4 afforded alpha- and beta-epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction conditions, and was found to be highly regioselective to give the preferential formation of 6-azido diol 6a/6b over 5-azido-diol 7a/7b. The 6-azido diol 6a/6b and 5-azido dial 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b. (C) 2010 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.tetasy.2010.01.007
作为产物：

描述：

3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖、二氯乙酸乙酯在 chromium dichloride 作用下，以四氢呋喃为溶剂，反应 3.0h，以87%的产率得到ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

参考文献：

名称：

铬介导的碳水化合物衍生的（E）-α，β-不饱和酯或酰胺的立体选择性合成

摘要：

据报道，铬介导的由碳水化合物衍生的二和三取代的（E）-α，β-不饱和酯或酰胺由一系列二氯酯或酰胺和各种糖醛合成。该过程以总的立体选择性和高收率进行。提出了一种基于顺序铬促进的醛醇型反应和完全立体选择性β-消除反应的机理来解释这些结果。