(3R,4R,5S)-4,5-Bis-benzyloxy-3-((R)-1,2-bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hex-1-en-3-ol

Base Information

Chemical Name:(3R,4R,5S)-4,5-Bis-benzyloxy-3-((R)-1,2-bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hex-1-en-3-ol
CAS No.:195304-44-0
Molecular Formula:C₄₂H₅₄O₆Si
Molecular Weight:682.973
Hs Code.:

Synonyms:(3R,4R,5S)-4,5-Bis-benzyloxy-3-((R)-1,2-bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hex-1-en-3-ol

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Chemical Property of (3R,4R,5S)-4,5-Bis-benzyloxy-3-((R)-1,2-bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hex-1-en-3-ol

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Technology Process of (3R,4R,5S)-4,5-Bis-benzyloxy-3-((R)-1,2-bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hex-1-en-3-ol

There total 7 articles about (3R,4R,5S)-4,5-Bis-benzyloxy-3-((R)-1,2-bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hex-1-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: 98.0%

: 1826-67-1
vinyl magnesium bromide

: 195304-43-9
(2R,4R,5S)-1,2,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-3-one

: 195304-44-0
(3R,4R,5S)-4,5-Bis-benzyloxy-3-((R)-1,2-bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hex-1-en-3-ol

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1016/S0040-4039(97)10407-5

Reference yield:

: 100-39-0
benzyl bromide

: 195304-44-0
(3R,4R,5S)-4,5-Bis-benzyloxy-3-((R)-1,2-bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hex-1-en-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / NaH / dimethylformamide / 5 h / Ambient temperature

2: 96 percent / 2N H₂SO₄ / acetic acid / 12 h / 60 °C

3: 90 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

4: 98 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

5: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -60 °C

6: 98 percent / tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(97)10407-5

Reference yield:

: 55902-93-7
methyl 3,5,6-tri-O-benzyl-α,β-D-glucofuranoside

: 195304-44-0
(3R,4R,5S)-4,5-Bis-benzyloxy-3-((R)-1,2-bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hex-1-en-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / NaH / dimethylformamide / 5 h / Ambient temperature

2: 96 percent / 2N H₂SO₄ / acetic acid / 12 h / 60 °C

3: 90 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

4: 98 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

5: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -60 °C

6: 98 percent / tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(97)10407-5