(3S,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dithian-2-yl-3,5,7-trimethyl-6-triphenylsilanyloxy-octanal

Base Information

Chemical Name:(3S,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dithian-2-yl-3,5,7-trimethyl-6-triphenylsilanyloxy-octanal
CAS No.:186692-75-1
Molecular Formula:C₃₉H₅₆O₃S₂Si₂
Molecular Weight:693.175
Hs Code.:

Synonyms:(3S,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dithian-2-yl-3,5,7-trimethyl-6-triphenylsilanyloxy-octanal

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Chemical Property of (3S,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dithian-2-yl-3,5,7-trimethyl-6-triphenylsilanyloxy-octanal

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Technology Process of (3S,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dithian-2-yl-3,5,7-trimethyl-6-triphenylsilanyloxy-octanal

There total 15 articles about (3S,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dithian-2-yl-3,5,7-trimethyl-6-triphenylsilanyloxy-octanal 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: 99.0%

: 186692-61-5
2-[(E)-(2R,3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-1,1,3,5-tetramethyl-2-triphenylsilanyloxy-hept-6-enyl]-[1,3]dithiane

: 186692-75-1
(3S,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dithian-2-yl-3,5,7-trimethyl-6-triphenylsilanyloxy-octanal

Guidance literature:: With toluene-4-sulfonic acid; In 1,4-dioxane; at 50 ℃;

Reference yield:

: 186692-74-0
(2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptan-1-ol

: 186692-75-1
(3S,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dithian-2-yl-3,5,7-trimethyl-6-triphenylsilanyloxy-octanal

Guidance literature:: Multi-step reaction with 3 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

1.2: 90 percent / Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: 99 percent / pTSA*H₂O / dioxane; H₂O / 2 h / 50 °C

With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 1.1: Condensation / 1.2: Elimination / 2.1: Wittig reaction / 3.1: Hydrolysis;
DOI:10.1021/ja971946k

Reference yield:

: 184297-54-9
(2S,3S,4R,5R)-1-Benzyloxy-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptan-3-ol

: 186692-75-1
(3S,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dithian-2-yl-3,5,7-trimethyl-6-triphenylsilanyloxy-octanal

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

3.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

3.2: 90 percent / Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C

5.1: 99 percent / pTSA*H₂O / dioxane; H₂O / 2 h / 50 °C

With 2,6-dimethylpyridine; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 1.1: silylation / 2.1: Oxidation / 3.1: Condensation / 3.2: Elimination / 4.1: Wittig reaction / 5.1: Hydrolysis;
DOI:10.1021/ja971946k