methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside
• CAS No.: 193271-74-8
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.289
• Mol file: 193271-74-8.mol

Synonyms:methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside

There total 6 articles about methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside 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:

methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (272113-74-3) → methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside (193271-74-8)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -98 ℃; for 0.25h;

DOI:10.1016/S0040-4039(97)10370-7

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside (193271-74-8)

Guidance literature:

Multi-step reaction with 5 steps

1: CSA / CHCl₃ / Heating

2: NaH, N-tosylimidazole / dimethylformamide / 2.5 h / Ambient temperature

3: benzene / 20 h / Ambient temperature

4: DIPEA, LiClO₄, DMAP, TsCl / acetonitrile / 16 h / 0 - 20 °C

5: DIBAL-H / CH₂Cl₂ / 0.25 h / -98 °C

With dmap; camphor-10-sulfonic acid; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; N-tosylimidazole; In dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(97)10370-7

Reference yield:

methyl 4,6-O-benzylidene-3-C-cyano-3-deoxy-α-D-altropyranoside (163580-26-5) → methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside (193271-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DIPEA, LiClO₄, DMAP, TsCl / acetonitrile / 16 h / 0 - 20 °C

2: DIBAL-H / CH₂Cl₂ / 0.25 h / -98 °C

With dmap; lithium perchlorate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(97)10370-7

upstream raw materials:

methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

benzaldehyde dimethyl acetal

methyl 4,6-O-benzylidene-3-C-cyano-3-deoxy-α-D-altropyranoside

methyl-alpha-D-glucopyranoside

Downstream raw materials:

(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde

C₂₀H₂₂O₆

(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-2-(1-oxopropyl)-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene

Methyl-4,6-O-benzyliden-2,3-dideoxy-3-C-hydroxymethyl-α-D-erythro-hex-2-enopyranosid