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

Base Information

• Chemical Name: methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• CAS No.: 272113-74-3
• Molecular Formula: C₁₅H₁₅NO₄
• Molecular Weight: 273.288
• Mol file: 272113-74-3.mol

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

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

There total 6 articles about methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-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-benzylidene-3-C-cyano-3-deoxy-α-D-altropyranoside (163580-26-5) → methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (272113-74-3)

Guidance literature:

With dmap; lithium perchlorate; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In acetonitrile; at 0 - 20 ℃; for 16h;

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

Reference yield:

C15H15O6NSOCH4 → methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (272113-74-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; at -30 ℃; for 2h;

DOI:10.1016/j.carres.2007.07.008

Reference yield:

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside (3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2,2880-96-8) → methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (272113-74-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃Al / toluene; tetrahydrofuran / 20 h / 23 °C

2: Et₃N / tetrahydrofuran / 1.5 h / -20 °C

3: 45.5 mg / DBU / CHCl₃ / 2 h / -30 °C

With triethylaluminum; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; chloroform; toluene;

DOI:10.1016/j.carres.2007.07.008

upstream raw materials:

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

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside

benzaldehyde dimethyl acetal

methyl-alpha-D-glucopyranoside

Downstream raw materials:

C₁₄H₁₁NO₃OCH₄O

(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

methyl 3-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

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