methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside

Base Information

• Chemical Name: methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside
• CAS No.: 149454-88-6
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348
• Mol file: 149454-88-6.mol

Synonyms:methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside

Chemical Property of methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside

There total 3 articles about methyl 2-O-benzyl-3,4-O-isopropylidene-β-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:

benzyl chloride (100-44-7) + methyl 3,4-O-isopropylidene-β-D-arabinopyranoside (4594-60-9,817620-70-5) → methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside (149454-88-6)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) DMF;

DOI:10.1248/cpb.41.636

Reference yield:

D-arabinopyranose (28697-53-2) → methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside (149454-88-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 9percent HCl / 15 h / Heating

2: p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h / 25 °C

3: NaH / dimethylformamide / 1 h / 25 °C

With hydrogenchloride; sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89611-3

Reference yield:

methyl-β-D-arabinopyranoside (5328-63-2) → methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside (149454-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h / 25 °C

2: NaH / dimethylformamide / 1 h / 25 °C

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89611-3

upstream raw materials:

benzyl chloride

methyl 3,4-O-isopropylidene-β-D-arabinopyranoside

D-arabinopyranose

methyl-β-D-arabinopyranoside

Downstream raw materials:

[(1R,2R,3R,4R)-4-(6-Amino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentyl]-methanol

Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester

Acetic acid (1R,2S,3R,4R,5R)-3-(6-benzoylamino-purin-9-yl)-4,5-bis-benzyloxy-2-nitro-cyclopentylmethyl ester

Acetic acid (1R,2R,3R,4R)-4-(6-benzoylamino-purin-9-yl)-2,3-bis-benzyloxy-cyclopentylmethyl ester