methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside

Base Information

• Chemical Name: methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside
• CAS No.: 1610594-24-5
• Molecular Formula: C₂₅H₃₂O₆
• Molecular Weight: 428.525
• Mol file: 1610594-24-5.mol

Synonyms:methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside

Chemical Property of methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside

There total 7 articles about methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside 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: 82.0%

methyl 4-C-allyl-2,3-di-O-benzyl-6-O-(p-methoxybenzyl)-4-o-methyl-α-D-galactopyranoside (1610594-23-4) → methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside (1610594-24-5)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 - 20 ℃; for 0.333333h;

DOI:10.1002/ejoc.201400028

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside (1610594-24-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 2 h / 60 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

3.1: trifluoroacetic acid; sodium cyanoborohydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Molecular sieve

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 - 0 °C / Inert atmosphere

5.1: tetrahydrofuran; diethyl ether / -78 °C / Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

7.1: ammonium cerium (IV) nitrate / acetonitrile; water / 0.33 h / 0 - 20 °C

With ammonium cerium (IV) nitrate; oxalyl dichloride; sodium hydride; camphor-10-sulfonic acid; sodium cyanoborohydride; dimethyl sulfoxide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 5.1: |Grignard Reaction;

DOI:10.1002/ejoc.201400028

Reference yield:

methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside (162680-20-8) → methyl 4-C-allyl-2,3-di-O-benzyl-4-O-methyl-α-D-galactopyranoside (1610594-24-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid; sodium cyanoborohydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Molecular sieve

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 - 0 °C / Inert atmosphere

4.1: tetrahydrofuran; diethyl ether / -78 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

6.1: ammonium cerium (IV) nitrate / acetonitrile; water / 0.33 h / 0 - 20 °C

With ammonium cerium (IV) nitrate; oxalyl dichloride; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 4.1: |Grignard Reaction;

DOI:10.1002/ejoc.201400028

upstream raw materials:

methyl-alpha-D-glucopyranoside

methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside

methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside

methyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-α-D-glucopyranoside

Downstream raw materials:

C₂₅H₃₀O₆

C₂₅H₂₈O₆

C₃₀H₄₀O₆Si

C₄₀H₅₂O₇Si