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

Base Information

Chemical Name:(2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptan-1-ol
CAS No.:186692-74-0
Molecular Formula:C₃₈H₅₆O₃S₂Si₂
Molecular Weight:681.164
Hs Code.:

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

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

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

There total 12 articles about (2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptan-1-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: 89.0%

: 186692-59-1
2-[(2R,3R,4S,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1,1,3,5-tetramethyl-2-triphenylsilanyloxy-hexyl]-[1,3]dithiane

: 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

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

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

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

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

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

With 2,6-dimethylpyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; 1: silylation / 2: Oxidation;
DOI:10.1021/ja971946k

Reference yield:

: 72486-93-2
1-methoxy-2-methyl-3-trimethylsiloxy-1,3-pentadiene

: 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

Guidance literature:: Multi-step reaction with 10 steps

1: TiCl₄ / CH₂Cl₂ / -78 °C

2: CSA / benzene / 20 °C

3: 91 percent / LiAlH₄ / diethyl ether / -78 °C

4: 93 percent / Et₂Zn / diethyl ether / 20 °C

5: N-iodosuccinimide / 20 °C

6: n-Bu₃SnH; AIBN / benzene / Heating

7: 97 percent / imidazole / dimethylformamide / 20 °C

8: 78 percent / TiCl₄ / CH₂Cl₂ / -78 - -40 °C

9: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; N-iodo-succinimide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; diethylzinc; tri-n-butyl-tin hydride; titanium tetrachloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: Cycloaddition / 2: acidolysis / 3: Reduction / 4: Cycloaddition / 5: Ring cleavage / 6: Dehalogenation / 7: silylation / 8: Condensation / 9: silylation / 10: Oxidation;
DOI:10.1021/ja971946k