(2Z,4S,5R,6S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4,6-dimethyl-2-trimethylsilanyl-hept-2-ene

Base Information

Chemical Name:(2Z,4S,5R,6S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4,6-dimethyl-2-trimethylsilanyl-hept-2-ene
CAS No.:444109-30-2
Molecular Formula:C₂₅H₄₆O₂Si₂
Molecular Weight:434.81
Hs Code.:

Synonyms:(2Z,4S,5R,6S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4,6-dimethyl-2-trimethylsilanyl-hept-2-ene

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Chemical Property of (2Z,4S,5R,6S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4,6-dimethyl-2-trimethylsilanyl-hept-2-ene

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Technology Process of (2Z,4S,5R,6S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4,6-dimethyl-2-trimethylsilanyl-hept-2-ene

There total 10 articles about (2Z,4S,5R,6S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4,6-dimethyl-2-trimethylsilanyl-hept-2-ene 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: 89.0%

: 444109-29-9
(1E,3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-iodo-1-trimethylsilanyl-hex-1-ene

: 5158-46-3
methylzinc chloride

: 444109-30-2
(2Z,4S,5R,6S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4,6-dimethyl-2-trimethylsilanyl-hept-2-ene

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethyl acetate; at 20 ℃; for 1h;
DOI:10.1021/ol016486l

Reference yield: 88.0%

: 75-16-1
methylmagnesium bromide

: 444109-29-9
(1E,3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-iodo-1-trimethylsilanyl-hex-1-ene

: 444109-30-2
(2Z,4S,5R,6S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4,6-dimethyl-2-trimethylsilanyl-hept-2-ene

Guidance literature:: methylmagnesium bromide; With zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.25h;

(1E,3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-iodo-1-trimethylsilanyl-hex-1-ene; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; at 20 ℃; for 2h;
DOI:10.1021/ja043168j

Reference yield:

: 444109-28-8
(3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne

: 444109-30-2
(2Z,4S,5R,6S)-7-benzyloxy-5-(tert-butyldimethylsilanyloxy)-4,6-dimethyl-2-trimethylsilanyl-hept-2-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: Cp₂Zr(H)Cl / tetrahydrofuran / 1.08 h / 20 - 55 °C

1.2: 92 percent / I₂ / tetrahydrofuran / 0.33 h / 20 °C

2.1: ZnCl₂ / tetrahydrofuran; diethyl ether / 0.25 h / 20 °C

2.2: 88 percent / Pd(PPh₃)4 / tetrahydrofuran; diethyl ether / 2 h / 20 °C

With Schwartz's reagent; zinc(II) chloride; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja043168j