1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside

Base Information

• Chemical Name: 1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside
• CAS No.: 693788-18-0
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347
• Mol file: 693788-18-0.mol

Synonyms:1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside

Chemical Property of 1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside

There total 5 articles about 1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-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:

2,2-dimethoxy-propane (77-76-9) + 4-methoxybenzyl α-L-arabinopyranoside (693787-87-0) → 1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside (693788-18-0)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200300723

Reference yield:

bromo-2,3,4-O-triacetyl-α/β-L-arabinopyranoside (51830-02-5) → 1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside (693788-18-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 49.8 g / I₂; Ag₂CO₃ / toluene

2: 75 percent / Et₃N / methanol; H₂O

3: 12.3 g / TsOH / dimethylformamide / 2 h / 20 °C

With iodine; toluene-4-sulfonic acid; triethylamine; silver carbonate; In methanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/ejoc.200300723

Reference yield:

L-(+)-arabinose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → 1-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-arabinopyranoside (693788-18-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 35 g / pyridine / 48 h / 0 °C

2: 21.7 g / HBr / acetic acid / 2 h / 20 °C

3: 49.8 g / I₂; Ag₂CO₃ / toluene

4: 75 percent / Et₃N / methanol; H₂O

5: 12.3 g / TsOH / dimethylformamide / 2 h / 20 °C

With pyridine; hydrogen bromide; iodine; toluene-4-sulfonic acid; triethylamine; silver carbonate; In methanol; water; acetic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1002/ejoc.200300723

upstream raw materials:

2,2-dimethoxy-propane

4-methoxybenzyl α-L-arabinopyranoside

bromo-2,3,4-O-triacetyl-α/β-L-arabinopyranoside

L-(+)-arabinose

Downstream raw materials:

acetic acid 6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

acetic acid 4,5-dihydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

acetic acid 4-allyloxy-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

acetic acid 4-allyloxy-2-(4-methoxy-benzyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl ester