(3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
• CAS No.: 191805-01-3
• Molecular Formula: C₂₆H₃₄O₆Si
• Molecular Weight: 470.638
• Mol file: 191805-01-3.mol

Synonyms:(3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Chemical Property of (3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

There total 4 articles about (3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl 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: 83.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (3aS,4R,6aR)-6a-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (191805-00-2) → (3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (191805-01-3)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;

DOI:10.1007/BF00807307

Reference yield:

3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside (70147-50-1) → (3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (191805-01-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / pyridine / 16 h / Ambient temperature

2: 71 percent / Me₃SiOSO₂CF₃ / 48 h / Ambient temperature

3: 88 percent / NaOMe / 1.5 h / Ambient temperature

4: 83 percent / imidazole, DMAP / dimethylformamide / 1.5 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In N,N-dimethyl-formamide;

DOI:10.1007/BF00807307

Reference yield:

(3-C-acetoxymethyl)-1-O-acetyl-2,3-O-isopropylidene-β-D-erythrofuranose (91738-40-8) → (3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (191805-01-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / Me₃SiOSO₂CF₃ / 48 h / Ambient temperature

2: 88 percent / NaOMe / 1.5 h / Ambient temperature

3: 83 percent / imidazole, DMAP / dimethylformamide / 1.5 h / Ambient temperature

With 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In N,N-dimethyl-formamide;

DOI:10.1007/BF00807307

upstream raw materials:

tert-butylchlorodiphenylsilane

(3aS,4R,6aR)-6a-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside

(3-C-acetoxymethyl)-1-O-acetyl-2,3-O-isopropylidene-β-D-erythrofuranose

Downstream raw materials:

(E)-3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-acrylic acid tert-butyl ester

3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

(3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid