6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: 6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol
• CAS No.: 247145-65-9
• Molecular Formula: C₁₉H₃₀O₄Si
• Molecular Weight: 350.53
• Mol file: 247145-65-9.mol

Synonyms:6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

Chemical Property of 6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

There total 4 articles about 6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol 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: 74.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3S)-6-Benzyloxy-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol → 6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol (247145-65-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1039/a904991f

Reference yield:

benzyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside (69247-18-3,81389-84-6,81389-85-7) → 6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol (247145-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / H₂O; K₂CO₃ / methanol / 1 h / 20 °C

2: 74 percent / NEt₃ / CH₂Cl₂ / 24 h / 20 °C

With water; potassium carbonate; triethylamine; In methanol; dichloromethane; 1: Hydrolysis / 2: Etherification;

DOI:10.1039/a904991f

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → 6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol (247145-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -20 - 20 °C

2: 93 percent / H₂O; K₂CO₃ / methanol / 1 h / 20 °C

3: 74 percent / NEt₃ / CH₂Cl₂ / 24 h / 20 °C

With boron trifluoride diethyl etherate; water; potassium carbonate; triethylamine; In methanol; dichloromethane; 1: Substitution / 2: Hydrolysis / 3: Etherification;

DOI:10.1039/a904991f

upstream raw materials:

tert-butyldimethylsilyl chloride

benzyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside

benzyl alcohol

D-glucal triacetate

Downstream raw materials:

(2S,3S,6S)-6-(tert-butyldimethylsilyloxymethyl)-3-(2,2,2-trichloroacetylamino)-2-(benzyloxy)-2H-3,6-dihydropyran