(3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one

Base Information

• Chemical Name: (3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one
• CAS No.: 847845-05-0
• Molecular Formula: C₂₁H₃₄O₄Si
• Molecular Weight: 378.584

Synonyms:(3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one

Chemical Property of (3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one

There total 5 articles about (3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one 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: 54.0%

(3R,4S,5R)-3-Benzyloxy-4-methoxy-5-vinyl-dihydro-furan-2-one (1046780-06-6) + methyllithium (917-54-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one (847845-05-0)

Guidance literature:

(3R,4S,5R)-3-Benzyloxy-4-methoxy-5-vinyl-dihydro-furan-2-one; methyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.25h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Further stages.;

DOI:10.1016/j.tet.2008.05.027

Reference yield: 54.0%

(3R,4S,5R)-3-Benzyloxy-5-hydroxy-4-methoxy-hept-6-en-2-one + tert-butyldimethylsilyl chloride (18162-48-6) → (3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one (847845-05-0)

Guidance literature:

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

DOI:10.1016/j.tetlet.2004.12.063

Reference yield:

(3R,4S,5R)-3-Benzyloxy-4-methoxy-5-vinyl-dihydro-furan-2-one (1046780-06-6) → (3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one (847845-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / -78 °C

2: 54 percent / imidazole / dimethylformamide

With 1H-imidazole; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2004.12.063

upstream raw materials:

tert-butyldimethylsilyl chloride

(3R,4S,5R)-3-Benzyloxy-4-methoxy-5-vinyl-dihydro-furan-2-one

5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-alpha-D-xylo-hex-5-enofuranose

benzyl bromide

Downstream raw materials:

(3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-hepta-1,6-diene

[(1S,2R,3S,4R,5R)-2-Allyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-methoxy-2-methyl-cyclopentyloxymethyl]-benzene

(3aR,4R,5S,6R,6aR)-4-Allyl-5-benzyloxy-6-methoxy-2,2,4-trimethyl-hexahydro-1-oxa-2-sila-pentalene

(1R,2R,3S,4S,5R)-2-allyl-3-benzyloxy-5-hydroxy-4-methoxy-2-methyl-cyclopentane-1-carboxylic acid methyl ester

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