(2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol

Base Information

• Chemical Name: (2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol
• CAS No.: 658052-78-9
• Molecular Formula: C₂₃H₃₂O₄Si
• Molecular Weight: 400.59

Synonyms:(2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol

Chemical Property of (2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol

There total 3 articles about (2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol 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: 95.0%

(2R,3S)-ethyl 2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate (658052-77-8) → (2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol (658052-78-9)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1002/hlca.200390302

Reference yield:

ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate (114185-07-8) → (2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol (658052-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 3 h / 0 - 20 °C

2: 35.39 g / LiBH₄ / diethyl ether; methanol / 3 h / 0 °C

With 1H-imidazole; lithium borohydride; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo0496291

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol (658052-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 3 h / 0 - 20 °C

2: 35.39 g / LiBH₄ / diethyl ether; methanol / 3 h / 0 °C

With 1H-imidazole; lithium borohydride; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo0496291

upstream raw materials:

(2R,3S)-ethyl 2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate

ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane

(4S,5S)-5-[(R)-(tert-Butyl-diphenyl-silanyloxy)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

(2S,3S,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester

(4R,5S)-5-[(R)-(tert-Butyl-diphenyl-silanyloxy)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

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