(2S,3S,5R)-2-((S)-3-Benzyloxy-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan

Base Information

Chemical Name:(2S,3S,5R)-2-((S)-3-Benzyloxy-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan
CAS No.:392663-08-0
Molecular Formula:C₃₈H₅₆O₄Si₂
Molecular Weight:633.031
Hs Code.:

Synonyms:(2S,3S,5R)-2-((S)-3-Benzyloxy-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan

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Chemical Property of (2S,3S,5R)-2-((S)-3-Benzyloxy-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan

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Technology Process of (2S,3S,5R)-2-((S)-3-Benzyloxy-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan

There total 8 articles about (2S,3S,5R)-2-((S)-3-Benzyloxy-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan 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%

: 392663-07-9
(2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan

: 392663-08-0
(2S,3S,5R)-2-((S)-3-Benzyloxy-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan

Guidance literature:: With hydrogen; nickel; In ethanol; at 25 ℃; for 1h;
DOI:10.1002/1521-3773(20011105)40

Reference yield: 91.0%

: 948297-39-0
C₃₂H₄₂O₄Si

: 18162-48-6
tert-butyldimethylsilyl chloride

: 392663-08-0
(2S,3S,5R)-2-((S)-3-Benzyloxy-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 20h;
DOI:10.1021/ja804659n

Reference yield:

: 157240-43-2
(4R)-4,5-isopropylidenedioxy-1-(dimethoxyphosphoryl)-2-pentanone

: 392663-08-0
(2S,3S,5R)-2-((S)-3-Benzyloxy-2-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan

Guidance literature:: Multi-step reaction with 7 steps

1.1: LiCl; N,N-diisopropylethylamine / acetonitrile / 2 h / 25 °C

1.2: 86 percent / acetonitrile / 15 h / 25 °C

2.1: 98 percent / LiI; LiAlH₄ / diethyl ether / -100 - 0 °C

3.1: 97 percent / AcOH / H₂O / 5 h / 40 °C

4.1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

5.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 25 °C

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 99 percent / H₂; Raney-Ni catalyst / ethanol / 1 h / 25 °C

With 2,6-dimethylpyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; Raney-Ni catalyst; hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium iodide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja0547477