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

Base Information

• Chemical Name: (2R,3S)-ethyl 2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate
• CAS No.: 658052-77-8
• Molecular Formula: C₂₅H₃₄O₅Si
• Molecular Weight: 442.627
• Mol file: 658052-77-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2R,3S)-ethyl 2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate 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: 100.0%

ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate (114185-07-8) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S)-ethyl 2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate (658052-77-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1016/j.tetasy.2009.09.022

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: 75.0%

(2R,3S)-ethyl 2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate (658052-77-8) → ethyl 2-(O-tert-butyldiphenylsilyl)-L-threonate (1202878-68-9)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; water; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetasy.2009.09.022

upstream raw materials:

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

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

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

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

(Z)-(S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester