methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanal)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanal)-α-D-glucopyranoside
• CAS No.: 557088-23-0
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456
• Mol file: 557088-23-0.mol

Synonyms:methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanal)-α-D-glucopyranoside

Chemical Property of methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanal)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanal)-α-D-glucopyranoside

There total 6 articles about methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanal)-α-D-glucopyranoside 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: 85.0%

methyl 2-O-benzyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside (365418-34-4) → methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanal)-α-D-glucopyranoside (557088-23-0)

Guidance literature:

methyl 2-O-benzyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside; With ozone; In dichloromethane; at -78 ℃;

With acetic acid; zinc; at -78 - 20 ℃;

DOI:10.1021/jo030039x

Reference yield:

Benzoic acid (2R,4aR,6S,7R,8S,8aR)-6-methoxy-8-phenoxythiocarbonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (365418-32-2) → methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanal)-α-D-glucopyranoside (557088-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 62 percent / AIBN / toluene / 4 h / Heating

2.1: NaH / methanol / 2 h / 20 °C

2.2: 94 percent / NaH / dimethylformamide / 12 h / 23 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: 85 percent / Zn; glacial acetic acid / -78 - 20 °C

With 2,2'-azobis(isobutyronitrile); sodium hydride; ozone; In methanol; dichloromethane; toluene;

DOI:10.1021/jo030039x

Reference yield:

methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside (365418-33-3) → methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanal)-α-D-glucopyranoside (557088-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / methanol / 2 h / 20 °C

1.2: 94 percent / NaH / dimethylformamide / 12 h / 23 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 85 percent / Zn; glacial acetic acid / -78 - 20 °C

With sodium hydride; ozone; In methanol; dichloromethane;

DOI:10.1021/jo030039x

upstream raw materials:

methyl 2-O-benzyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside

methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside

Benzoic acid (2R,4aR,6S,7R,8S,8aR)-6-methoxy-8-phenoxythiocarbonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanoic acid)-α-D-glucopyranoside

((2R,4aR,6S,7R,8S,8aS)-7-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

(2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-2-((2R,4aR,6S,7R,8S,8aS)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ylmethyl)-6-benzyloxymethyl-tetrahydro-pyran-3-ol

(2R,4aR,6S,7R,8S,8aS)-7-Benzyloxy-8-[2-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-allyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine