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

Base Information

• Chemical Name: Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(2-methoxyethyl)-2-C-vinyl-α-D-ribo-hexopyranoside
• CAS No.: 78342-35-5
• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.412
• Mol file: 78342-35-5.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(2-methoxyethyl)-2-C-vinyl-α-D-ribo-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:

Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-ribo-hexopyranoside (78342-34-4) → Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(2-methoxyethyl)-2-C-vinyl-α-D-ribo-hexopyranoside (78342-35-5)

Guidance literature:

DOI:10.1021/jo00331a050

Reference yield:

methyl 4,6-O-(phenylmethylene)-3-deoxy-α-D-erythro-hexopyranoside-2-ulose (74524-02-0) → Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(2-methoxyethyl)-2-C-vinyl-α-D-ribo-hexopyranoside (78342-35-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / acetonitrile / Heating

2: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

3: mercuric trifluoroacetate / 10 h

4: 0.9 g / benzonitrile / 2 h / Heating

5: LiAlH₄, NaH / dimethylformamide / 0.5 h / 0 °C

6: 0.36 g / 0.5 h

With lithium aluminium tetrahydride; mercury(II) trifluoroacetate; sodium hydride; In diethyl ether; benzonitrile; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00187a010

Reference yield:

Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside (78342-32-2) → Methyl 4,6-O-Benzylidene-2,3-dideoxy-2-C-(2-methoxyethyl)-2-C-vinyl-α-D-ribo-hexopyranoside (78342-35-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / acetonitrile / Heating

2: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

3: 90 percent / mercuric trifluoroacetate

4: 85 percent / benzonitrile / Heating

With lithium aluminium tetrahydride; mercury(II) trifluoroacetate; In diethyl ether; benzonitrile; acetonitrile;

DOI:10.1021/jo00187a010

upstream raw materials:

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

Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside

methyl iodide

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

Refernces

• 1、 Fraser-Reid, Bert,Tsang, Raymond,Tulshian, Deen Bundhu,Sun, King Mo. "Highly Stereoselective Routes to Functionalized Geminal Alkyl Derivatives of Carbohydrates". . p. 3764 - 3767. Retrieved 2007/10/02.