(4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one

Base Information

Chemical Name:(4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one
CAS No.:807364-57-4
Molecular Formula:C₄₄H₇₀O₆Si₂
Molecular Weight:751.207
Hs Code.:

(4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one

Synonyms:(4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one

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Chemical Property of (4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one

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Technology Process of (4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one

There total 12 articles about (4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one 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: 73.0%

: 807364-52-9
dimethyl (4S)-4-benzyloxy-3,3-dimethyl-2-oxohept-6-en-1-ylphosphonate

: 807364-12-1
(E,5R)-5-tert-butyldimethylsilyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-6-(4-methoxybenzyloxy)hexanal

: 807364-57-4
(4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one

Guidance literature:: dimethyl (4S)-4-benzyloxy-3,3-dimethyl-2-oxohept-6-en-1-ylphosphonate; With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

(E,5R)-5-tert-butyldimethylsilyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-6-(4-methoxybenzyloxy)hexanal; In acetonitrile; at 20 ℃; for 21h; Inert atmosphere;
DOI:10.1039/c6ob01804a

Reference yield:

: 214914-80-4
methyl (5R)-5-hydroxy-6-(4-methoxybenzyloxy)hex-2-ynoate

: 807364-57-4
(4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one

Guidance literature:: Multi-step reaction with 6 steps

1: LiCl / CuCl / -78 °C

2: DIBAL-H / tetrahydrofuran

3: 2,6-lutidine / tetrahydrofuran

4: 70 percent / ADmix β; OsO4 / butan-1-ol; H2O

5: 100 percent / NaIO₄ / methanol

6: 71 percent / LiCl; iPr₂NEt / acetonitrile

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; diisobutylaluminium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; lithium chloride; copper(l) chloride; In tetrahydrofuran; methanol; water; acetonitrile; butan-1-ol;
DOI:10.1016/j.tetlet.2004.09.124

Reference yield:

: (S)-3-Benzyloxy-2,2-dimethyl-hex-5-enal

: 807364-57-4
(4S,7E,12R)-4-benzyloxy-12-tert-butyldimethylsilyloxy-10-[(Z)-2-tert-butyldimethylsilyloxyethylidene]-13-(4-methoxybenzyloxy)-5,5-dimethyltrideca-1,7-dien-6-one

Guidance literature:: Multi-step reaction with 3 steps

1: nBuLi

2: Dess-Martin periodinane

3: 71 percent / LiCl; iPr₂NEt / acetonitrile

With n-butyllithium; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile;
DOI:10.1016/j.tetlet.2004.09.124