(3S,4S,5R,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-8-trityloxy-oct-1-en-4-ol

Base Information

Chemical Name:(3S,4S,5R,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-8-trityloxy-oct-1-en-4-ol
CAS No.:850211-65-3
Molecular Formula:C₃₆H₅₀O₃Si
Molecular Weight:558.877
Hs Code.:

Synonyms:(3S,4S,5R,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-8-trityloxy-oct-1-en-4-ol

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Chemical Property of (3S,4S,5R,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-8-trityloxy-oct-1-en-4-ol

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Technology Process of (3S,4S,5R,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-8-trityloxy-oct-1-en-4-ol

There total 6 articles about (3S,4S,5R,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-8-trityloxy-oct-1-en-4-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: 82.0%

: 850211-64-2
(2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-5-trityloxy-pentanal

: C₂₄H₃₇B

: 850211-65-3
(3S,4S,5R,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-8-trityloxy-oct-1-en-4-ol

Guidance literature:: (2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-5-trityloxy-pentanal; C₂₄H₃₇B; With boron trifluoride diethyl etherate; In tetrahydrofuran; for 7.5h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 - 60 ℃; for 4h;

Reference yield:

: 850211-63-1
(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-5-trityloxy-pentan-1-ol

: 850211-65-3
(3S,4S,5R,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-8-trityloxy-oct-1-en-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridine*SO₂; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 3 h / 20 °C

2.1: tetrahydrofuran / 7 h / -78 °C

2.2: 1.25 g / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 4 h / 60 °C

With sulfur(IV) oxide * pyridine; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 2.1: Brown crootylation;
DOI:10.1021/ol050455z

Reference yield:

: 850211-61-9
(S)-4-Benzyl-3-((2S,3R,4S)-3-hydroxy-2,4-dimethyl-5-trityloxy-pentanoyl)-oxazolidin-2-one

: 850211-65-3
(3S,4S,5R,6R,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7-trimethyl-8-trityloxy-oct-1-en-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2.1: 80 percent / LiBH₄; EtOH / tetrahydrofuran / 13 h / 0 - 20 °C

3.1: pyridine*SO₂; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 3 h / 20 °C

4.1: tetrahydrofuran / 7 h / -78 °C

4.2: 1.25 g / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 4 h / 60 °C

With 2,6-dimethylpyridine; lithium borohydride; ethanol; sulfur(IV) oxide * pyridine; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 4.1: Brown crootylation;
DOI:10.1021/ol050455z