(2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol

Base Information

• Chemical Name: (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol
• CAS No.: 172532-53-5
• Molecular Formula: C₂₂H₃₈O₅Si
• Molecular Weight: 410.626

Synonyms:(2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol

Chemical Property of (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol

There total 2 articles about (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol 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:

(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol → (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol (172532-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) -78 deg C, 3 h

2: 1.) 4 Angstroem mol. sieves, MgBr₂*Et₂O, 2.) DIBALH / 1.) Et₂O, -78 deg C, 15 min, 2.) toluene, -78 deg C, 15 min

With oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; magnesium bromide;

DOI:10.1021/jo00129a029

Reference yield:

allyltributylstanane (24850-33-7) + (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-propionaldehyde (152669-29-9) → (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol (172532-53-5) + (2S,3S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol (172326-96-4)

Guidance literature:

With 4 A molecular sieve; magnesium bromide; Yield given. Multistep reaction; 1) CH₂Cl₂, room temp., 15 min; -78 deg C, 10 min, 2.) -78 deg C, 2 h; -78 deg C to -40 deg C, 1.5 h;

DOI:10.1021/jo00129a029

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol (172532-53-5) → 1-[(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-triisopropylsilanyloxy-hex-5-enyloxymethoxymethyl]-4-methoxy-benzene

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; for 2h;

DOI:10.1021/jo00129a029

upstream raw materials:

allyltributylstanane

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-propionaldehyde

Downstream raw materials:

(2R,3R)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-hex-5-enal

(2R,3R)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-hex-5-en-1-ol

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