1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

Base Information

• Chemical Name: 1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside
• CAS No.: 135214-83-4
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268
• Mol file: 135214-83-4.mol

Synonyms:1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

Chemical Property of 1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

There total 4 articles about 1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside 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: 66.0%

benzaldehyde dimethyl acetal (1125-88-8) + (3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran (3971-47-9,7103-29-9,13035-11-5,26242-03-5) → 1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside (135214-83-4)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 27h; Ambient temperature;

DOI:10.1021/jo00070a039

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) + 1,2-dideoxy-D-allose (7103-29-9) → 1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside (135214-83-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/jm990422n

Reference yield:

3,4,6-tri-O-acetyl-1,2-dideoxy-D-glucopyranose (13035-12-6,53269-94-6,53735-78-7) → 1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside (135214-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate; methanol

2: 115 °C

With methanol; sodium methylate;

upstream raw materials:

benzaldehyde

(3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran

benzaldehyde dimethyl acetal

1,2-dideoxy-D-allose

Downstream raw materials:

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((2R,4aR,8R,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-4-yl ester

(2R,4aR,8R,8aS)-8-(2-Methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

(2R,4aR,8aR)-2-Phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

3-O-benzoyl-4,6-O-benzylidene-1,2-dideoxy-D-glucopyranose