4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Base Information

• Chemical Name: 4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• CAS No.: 639807-52-6
• Molecular Formula: C₃₇H₄₉ClO₁₄
• Molecular Weight: 753.241
• Mol file: 639807-52-6.mol

Synonyms:

Chemical Property of 4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

There total 4 articles about 4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 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:

2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal (72200-51-2) → 4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (639807-52-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / CH₂Cl₂ / 24 h / 20 °C

2.1: NaH / dimethylformamide / 3 h / 0 - 20 °C

2.2: 78 percent / dimethylformamide / 0.75 h / 20 °C

3.1: CH₂Cl₂ / 2.5 h / 0 °C

With pyridine; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2003.08.001

Reference yield:

benzyl bromide (100-39-0) → 4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (639807-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 3 h / 0 - 20 °C

1.2: 78 percent / dimethylformamide / 0.75 h / 20 °C

2.1: CH₂Cl₂ / 2.5 h / 0 °C

With sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2003.08.001

Reference yield:

4-O-(3,4-O-isopropylidene-6-O-p-toluenesulfonyl-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (639807-48-0) → 4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (639807-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 3 h / 0 - 20 °C

1.2: 78 percent / dimethylformamide / 0.75 h / 20 °C

2.1: CH₂Cl₂ / 2.5 h / 0 °C

With sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2003.08.001

upstream raw materials:

3-chloro-benzenecarboperoxoic acid

4-O-(2-O-benzyl-6-deoxy-3,4-O-isopropylidene-α-L-arabino-hex-5-enopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal

benzyl bromide

Downstream raw materials:

2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal