Methyl 4,6-O-Benzylidene-2-C-((E)-carbethoxymethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside

Base Information

• Chemical Name: Methyl 4,6-O-Benzylidene-2-C-((E)-carbethoxymethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside
• CAS No.: 104833-45-6
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.369
• Mol file: 104833-45-6.mol

Synonyms:Methyl 4,6-O-Benzylidene-2-C-((E)-carbethoxymethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside

Chemical Property of Methyl 4,6-O-Benzylidene-2-C-((E)-carbethoxymethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 4,6-O-Benzylidene-2-C-((E)-carbethoxymethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside

There total 2 articles about Methyl 4,6-O-Benzylidene-2-C-((E)-carbethoxymethylene)-2,3-dideoxy-α-D-erythro-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: 90.0%

methyl 4,6-O-(phenylmethylene)-3-deoxy-α-D-erythro-hexopyranoside-2-ulose (74524-02-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → Methyl 4,6-O-Benzylidene-2-C-((E)-carbethoxymethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside (104833-45-6)

Guidance literature:

In acetonitrile; Heating;

DOI:10.1021/jo00187a010

Reference yield:

methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside (72904-78-0) → Methyl 4,6-O-Benzylidene-2-C-((E)-carbethoxymethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside (104833-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / dimethylsulfoxide, trifluoroacetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

2: 90 percent / acetonitrile / Heating

With dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; acetonitrile;

DOI:10.1021/jo00187a010

Reference yield: 90.0%

Methyl 4,6-O-Benzylidene-2-C-((E)-carbethoxymethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside (104833-45-6) → Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-((hydroxymethyl)methylene)-α-D-erythro-hexopyranoside (89872-88-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/jo00187a010

upstream raw materials:

methyl 4,6-O-(phenylmethylene)-3-deoxy-α-D-erythro-hexopyranoside-2-ulose

ethyl (triphenylphosphoranylidene)acetate

methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside

Downstream raw materials:

Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-((hydroxymethyl)methylene)-α-D-erythro-hexopyranoside

Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(2-methoxyethyl)-2-C-vinyl-α-D-ribo-hexopyranoside

Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-ribo-hexopyranoside

Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(((vinyloxy)methyl)methylene)-α-D-erythro-hexopyranoside