(E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-1-hydroxy-6-((4-methoxybenzyl)oxy)octan-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

Base Information

Chemical Name:(E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-1-hydroxy-6-((4-methoxybenzyl)oxy)octan-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate
CAS No.:1261422-97-2
Molecular Formula:C₃₇H₅₈O₈Si
Molecular Weight:658.948
Hs Code.:

Synonyms:(E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-1-hydroxy-6-((4-methoxybenzyl)oxy)octan-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

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Chemical Property of (E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-1-hydroxy-6-((4-methoxybenzyl)oxy)octan-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

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Technology Process of (E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-1-hydroxy-6-((4-methoxybenzyl)oxy)octan-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

There total 14 articles about (E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-1-hydroxy-6-((4-methoxybenzyl)oxy)octan-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

: (E)-(4R,6R,7R)-7-((benzyloxy)methoxy)-6-((4-methoxybenzyl)oxy)oct-1-en-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

: 1261422-97-2
(E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-1-hydroxy-6-((4-methoxybenzyl)oxy)octan-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

Guidance literature:: (E)-(4R,6R,7R)-7-((benzyloxy)methoxy)-6-((4-methoxybenzyl)oxy)oct-1-en-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; for 0.916667h; Sonication;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;

Reference yield: 74.0%

: 1261422-95-0
(E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-6-((4-methoxybenzyl)oxy)oct-1-en-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

: 1261422-97-2
(E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-1-hydroxy-6-((4-methoxybenzyl)oxy)octan-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

Guidance literature:: (E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-6-((4-methoxybenzyl)oxy)oct-1-en-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; Inert atmosphere; Sonication;

With water; dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ja110198y

Reference yield:

: 122520-56-3
(E)-methyl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

: 1261422-97-2
(E)-(4S,6R,7R)-7-((benzyloxy)methoxy)-1-hydroxy-6-((4-methoxybenzyl)oxy)octan-4-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: water; sodium hydroxide / ethanol / 15 h / 0 °C

2.1: dmap; 4-(dimethylamino)pyridine hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C / Inert atmosphere; Sonication

3.2: 1 h / 0 °C / Inert atmosphere

With dmap; water; 4-(dimethylamino)pyridine hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/ja110198y