tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranoside

Base Information

• Chemical Name: tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranoside
• CAS No.: 131013-38-2
• Molecular Formula: C₂₈H₄₆O₈Si
• Molecular Weight: 538.754
• Mol file: 131013-38-2.mol

Synonyms:tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranoside

Chemical Property of tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranoside

There total 10 articles about tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranoside 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: 92.0%

tert-Butyldimethylsilyl 4-O-Acetyl-2,6-dideoxy-α-D-lyxo-pyranoside (131041-38-8) + (2R,3S,4R)-4-Benzyloxy-3-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran (106023-22-7,106023-23-8) → tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-β-D-lyxo-pyranoside (131013-40-6) + tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranoside (131013-38-2)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; acetonitrile; 1) -42 deg C, 50 min, 2) 23 deg C, 10 min;

DOI:10.1021/jo00004a054

Reference yield: 79.0%

tert-Butyldimethylsilyl 4-O-Acetyl-2,6-dideoxy-β-D-lyxo-pyranoside (131013-47-3) + (2R,3S,4R)-4-Benzyloxy-3-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran (106023-22-7,106023-23-8) → tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-β-D-lyxo-pyranosyl)-2,6-dideoxy-β-D-lyxo-pyranoside (131013-41-7) + tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranoside (131013-38-2)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; acetonitrile; 1) -42 deg C, 50 min, 2) 23 deg C, 10 min;

DOI:10.1021/jo00004a054

Reference yield:

tert-Butyldimethylsilyl 4-O-Acetyl-3-O-benzyl-2,6-dideoxy-D-lyxo-pyranoside (131013-35-9,131013-46-2) → tert-Butyldimethylsilyl 4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranoside (131013-38-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / ethanol / 48 h / 23 °C / 760 Torr

2: 92 percent / NBS / acetonitrile; tetrahydrofuran / 1) -42 deg C, 50 min, 2) 23 deg C, 10 min

With N-Bromosuccinimide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; acetonitrile;

DOI:10.1021/jo00004a054

upstream raw materials:

tert-Butyldimethylsilyl 4-O-Acetyl-2,6-dideoxy-α-D-lyxo-pyranoside

(2R,3S,4R)-4-Benzyloxy-3-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran

tert-Butyldimethylsilyl 4-O-Acetyl-2,6-dideoxy-β-D-lyxo-pyranoside

methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside

Downstream raw materials:

4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-β-D-lyxo-pyranose

4-O-Acetyl-3-(3-O-benzyl-2,6-dideoxy-4-O-methyl-α-D-lyxo-pyranosyl)-2,6-dideoxy-α-D-lyxo-pyranose