4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

Base Information

• Chemical Name: 4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide
• CAS No.: 88180-37-4
• Molecular Formula: C₁₄H₁₃NO₃
• Molecular Weight: 243.262
• Mol file: 88180-37-4.mol

Synonyms:4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

Chemical Property of 4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

There total 3 articles about 4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide 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:

((2R,3S,6S)-3-acetoxy-6-cyano-3,6-dihydro-2H-pyran-2-yl)methyl acetate (83938-00-5) → 4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide (88180-37-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Amberlyst 15 / methanol / 24 h / Heating

2: Amberlyst 15 / CHCl₃ / 22.5 h

With Amberlyst 15; In methanol; chloroform;

DOI:10.1055/s-2002-33527

Reference yield:

D-glucal triacetate (2873-29-2) → 4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide (88180-37-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / SnCl₄ / CH₂Cl₂ / 0.33 h / -78 - -20 °C

2: Amberlyst 15 / methanol / 24 h / Heating

3: Amberlyst 15 / CHCl₃ / 22.5 h

With Amberlyst 15; tin(IV) chloride; In methanol; dichloromethane; chloroform;

DOI:10.1055/s-2002-33527

Reference yield:

2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide (88180-36-3) + benzaldehyde (100-52-7) → 4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide (88180-37-4)

Guidance literature:

With zinc(II) chloride; for 3h;

DOI:10.1021/jo00177a026

upstream raw materials:

2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

benzaldehyde

((2R,3S,6S)-3-acetoxy-6-cyano-3,6-dihydro-2H-pyran-2-yl)methyl acetate

D-glucal triacetate

Downstream raw materials:

5,7-O-Benzylidene-2,6-anhydro-3,4-dideoxy-aldehydo-D-erythro-hept-2-enose

5,7-O-Benzylidene-2,6-anhydro-3,4-dideoxy-D-arabino-hept-3-enitol

Chloro-methanesulfonic acid (2R,4S,5R)-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxan-4-ylmethyl ester

Chloro-methanesulfonic acid (2R,4S,5R)-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyloxy]-2-phenyl-[1,3]dioxan-4-ylmethyl ester