1-O-benzyl-2,3-O-bis(methylcarbonate)-5-O-tert-butyldimethylsilyl-β-D-ribofuranose

Base Information

• Chemical Name: 1-O-benzyl-2,3-O-bis(methylcarbonate)-5-O-tert-butyldimethylsilyl-β-D-ribofuranose
• CAS No.: 1450757-02-4
• Molecular Formula: C₂₂H₃₄O₉Si
• Molecular Weight: 470.592

Synonyms:1-O-benzyl-2,3-O-bis(methylcarbonate)-5-O-tert-butyldimethylsilyl-β-D-ribofuranose

Chemical Property of 1-O-benzyl-2,3-O-bis(methylcarbonate)-5-O-tert-butyldimethylsilyl-β-D-ribofuranose

Chemical Property:

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Technology Process of 1-O-benzyl-2,3-O-bis(methylcarbonate)-5-O-tert-butyldimethylsilyl-β-D-ribofuranose

There total 2 articles about 1-O-benzyl-2,3-O-bis(methylcarbonate)-5-O-tert-butyldimethylsilyl-β-D-ribofuranose 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%

1-O-benzyl-5-O-tert-butyldimethylsilyl-β-D-ribofuranose (80235-51-4) + methyl chloroformate (79-22-1) → 1-O-benzyl-2,3-O-bis(methylcarbonate)-5-O-tert-butyldimethylsilyl-β-D-ribofuranose (1450757-02-4)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 ℃;

DOI:10.1039/c3ob41016a

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1-O-benzyl-2,3-O-bis(methylcarbonate)-5-O-tert-butyldimethylsilyl-β-D-ribofuranose (1450757-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; pyridine / dichloromethane / 18 h / 0 °C / Inert atmosphere

2: dmap; pyridine / dichloromethane / 0 °C

With pyridine; dmap; In dichloromethane;

DOI:10.1039/c3ob41016a

Reference yield: 91.0%

1-O-benzyl-2,3-O-bis(methylcarbonate)-5-O-tert-butyldimethylsilyl-β-D-ribofuranose (1450757-02-4) → 1-O-benzyl-2,3-O-bis(methylcarbonate)-β-D-ribofuranose (1450757-05-7)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; for 3h;

DOI:10.1039/c3ob41016a

upstream raw materials:

tert-butyldimethylsilyl chloride

1-O-benzyl-5-O-tert-butyldimethylsilyl-β-D-ribofuranose

methyl chloroformate

Downstream raw materials:

1-O-benzyl-2,3-O-bis(methylcarbonate)-β-D-ribofuranose

5-O-dibenzylphosphate-1-O-benzyl-2,3-O-bis(methylcarbonate)-β-D-ribofuranose

5-O-phosphate-1-O-benzyl-2,3-O-bis(methylcarbonate)-β-D-ribofuranose

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