methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside

Base Information

• Chemical Name: methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside
• CAS No.: 1394848-29-3
• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.434
• Mol file: 1394848-29-3.mol

Synonyms:methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside

Chemical Property of methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside

There total 2 articles about methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside 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: 86.0%

methyl 3,5-di-O-benzyl-2-methylene-α-D-ribofuranoside (1394848-32-8) → methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside (1394848-29-3)

Guidance literature:

methyl 3,5-di-O-benzyl-2-methylene-α-D-ribofuranoside; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

With sodium peroxoborate tetrahydrate; water; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1039/c2cc34556k

Reference yield:

(2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one (885592-69-8) → methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside (1394848-29-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere

1.2: 72 h / -78 - 20 °C / Inert atmosphere

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; sec.-butyllithium; In tetrahydrofuran; cyclohexane; 1.2: Wittig reaction / 2.1: Hydroboration reaction;

DOI:10.1039/c2cc34556k

Reference yield: 90.0%

phthalimide (136918-14-4,85-41-6) + methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside (1394848-29-3) → methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside (1394848-33-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1039/c2cc34556k

upstream raw materials:

(2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one

methyl 3,5-di-O-benzyl-2-methylene-α-D-ribofuranoside

Downstream raw materials:

methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside

methyl 3,5-di-O-benzyl-2-deoxy-2-α-[(α,α,α-trifluoroacetyl)aminomethyl]-α-D-ribofuranoside

3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine

3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine