benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside

Base Information

• Chemical Name: benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside
• CAS No.: 115983-66-9
• Molecular Formula: C₁₉H₃₂O₄Si
• Molecular Weight: 352.546
• Mol file: 115983-66-9.mol

Synonyms:benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside

Chemical Property of benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside

There total 4 articles about benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside 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: 13.0%

dimethylmagnesium (2999-74-8) + benzyl 2,3-anhydro-4-O-(tert-butyldimethylsilyl)-α-D-ribopyranoside (115983-58-9) → benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside (115983-66-9) + benzyl 3-deoxy-3-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-xylopyranoside (115983-67-0)

Guidance literature:

In diethyl ether; for 24h; Title compound not separated from byproducts; Heating;

DOI:10.1021/jo00254a023

Reference yield:

Benzyl 2,3-anhydro-α-D-ribopyranoside (61134-24-5) → benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside (115983-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / imidazole / dimethylformamide / 0.83 h / 35 °C

2: 1.) cuprous iodide / 1.) diethyl ether, -40 deg C, 5 min, 2.) 0 deg C, 0.6 h

With 1H-imidazole; copper(l) iodide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00254a023

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside (115983-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / imidazole / dimethylformamide / 0.83 h / 35 °C

2: 1.) cuprous iodide / 1.) diethyl ether, -40 deg C, 5 min, 2.) 0 deg C, 0.6 h

With 1H-imidazole; copper(l) iodide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00254a023

upstream raw materials:

methyllithium

trimethylaluminum

benzyl 2,3-anhydro-4-O-(tert-butyldimethylsilyl)-α-D-ribopyranoside

dimethylmagnesium

Downstream raw materials:

(2R,3S,4S,5R/S)-5-O-benzyl-4-methyl-2-O-(tert-butyldimethylsilyl)dec-6-yne-1,2,3,5-tetrol

benzyl 2-deoxy-2-C-methyl-α-D-arabinopyranoside

((2R,3S,4R)-2-Benzyloxy-3-methyl-tetrahydro-pyran-4-yloxy)-tert-butyl-dimethyl-silane

(3R,4S,5S,6S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-3-ol