Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester

Base Information

Chemical Name:Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester
CAS No.:499121-76-5
Molecular Formula:C₂₇H₃₈O₅Si
Molecular Weight:470.681
Hs Code.:

Synonyms:Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester

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Chemical Property of Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester

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Technology Process of Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester

There total 6 articles about Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester 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: 84.0%

: 75-36-5
acetyl chloride

: 499121-75-4
(2S,3S,5S)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(3-hydroxy-propyl)-tetrahydro-furan-3-ol

: 499121-76-5
Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester

Guidance literature:: With 2,3,5-trimethyl-pyridine; In dichloromethane; at 0 - 7 ℃;
DOI:10.1021/jo026302w

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 499121-76-5
Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: 65 percent / BH₃*Me₂S; 2-methyl-2-butene / tetrahydrofuran / 0 - 20 °C

3: 84 percent / collidine / CH₂Cl₂ / 0 - 7 °C

With 2,3,5-trimethyl-pyridine; dmap; 2-methyl-but-2-ene; dimethylsulfide borane complex; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo026302w

Reference yield:

: Acetic acid (3aS,6aS)-5-oxo-hexahydro-furo[3,2-b]furan-2-yl ester

: 499121-76-5
Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: BF₃*Et₂O / acetonitrile / 2.33 h / 0 - 20 °C

2: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

3: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4: 65 percent / BH₃*Me₂S; 2-methyl-2-butene / tetrahydrofuran / 0 - 20 °C

5: 84 percent / collidine / CH₂Cl₂ / 0 - 7 °C

With 2,3,5-trimethyl-pyridine; dmap; lithium aluminium tetrahydride; 2-methyl-but-2-ene; dimethylsulfide borane complex; boron trifluoride diethyl etherate; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo026302w