(S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Base Information

• Chemical Name: (S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester
• CAS No.: 648433-06-1
• Molecular Formula: C₅₀H₅₈O₁₀Si
• Molecular Weight: 847.09
• Mol file: 648433-06-1.mol

Synonyms:(S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Chemical Property of (S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

There total 5 articles about (S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric 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: 85.0%

(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate (124655-05-6) + 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (125164-10-5) → (S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (648433-06-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -50 - 20 ℃;

DOI:10.1016/j.tetlet.2003.10.047

Reference yield:

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose (4356-77-8,35094-65-6,61277-56-3,65556-30-1,78185-13-4,78185-15-6,109958-31-8,109958-33-0,113532-02-8,59433-13-5) → (S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (648433-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / benzylamine / 3 h / 20 °C

2: 75 percent / NaH / CH₂Cl₂ / 3 h / 20 °C

3: 85 percent / trimethylsilyl triflate / acetonitrile; CH₂Cl₂ / -50 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; benzylamine; In dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2003.10.047

Reference yield:

dimethyl (S)-malate (617-55-0) → (S)-3-((3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (648433-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / BH₃*Me₂S; NaBH₄ / tetrahydrofuran / 4 °C

2: 90 percent / imidazole / dimethylformamide / 12 h / 20 °C

3: 85 percent / trimethylsilyl triflate / acetonitrile; CH₂Cl₂ / -50 - 20 °C

With 1H-imidazole; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetlet.2003.10.047

upstream raw materials:

(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

dimethyl (S)-malate

Downstream raw materials:

(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-butyric acid