methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methtyl-D-manno-oct-2-(E)-enoate

Base Information

• Chemical Name: methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methtyl-D-manno-oct-2-(E)-enoate
• CAS No.: 72079-88-0
• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.423
• Mol file: 72079-88-0.mol

Synonyms:methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methtyl-D-manno-oct-2-(E)-enoate

Chemical Property of methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methtyl-D-manno-oct-2-(E)-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methtyl-D-manno-oct-2-(E)-enoate

There total 15 articles about methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methtyl-D-manno-oct-2-(E)-enoate 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: 93.0%

4,6-O-benzylidene-2,3-dideoxy-2,3-C-isopropylidene-aldehydo-D-mannose (72079-87-9) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methtyl-D-manno-oct-2-(E)-enoate (72079-88-0)

Guidance literature:

In dichloromethane; for 1.5h;

DOI:10.1016/S0040-4020(01)82414-5

Reference yield: 83.0%

4,6-O-benzylidene-2,3-dideoxy-2,3-C-isopropylidene-D-glucose (72120-96-8) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methyl-D-gluco-oct-2-(Z)-enoate (72120-99-1) + methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methyl-D-gluco-oct-2-(E)-enoate (72079-88-0,72120-99-1,92541-94-1,92541-95-2,92541-96-3)

Guidance literature:

In dichloromethane; for 1h;

DOI:10.1016/S0040-4020(01)82414-5

Reference yield:

methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-C--α-D-mannopyranoside (72079-84-6) → methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methyl-D-gluco-oct-2-(E)-enoate (72079-88-0,72120-99-1,92541-94-1,92541-95-2,92541-96-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 46 percent / Et₂N / CH₂Cl₂ / 1 h / -78 °C

2: 95 percent / lithium aluminum hydride / diethyl ether / 14 h / Ambient temperature

3: H₂O / dioxane / 1.5 h / Heating

4: 94 percent / sodium methoxide / methanol / 12 h

5: 83 percent / CH₂Cl₂ / 1 h

With lithium aluminium tetrahydride; water; sodium methylate; diethylamine; In 1,4-dioxane; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(01)82414-5

upstream raw materials:

4,6-O-benzylidene-2,3-dideoxy-2,3-C-isopropylidene-D-glucose

methyl 2-(triphenylphosphoranylidene)propionate

methyl 4,6-O-(phenylmethylene)-2,3-dideoxy-2,3-C-isopropylidene-α-D-mannopyranoside

methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-C--α-D-mannopyranoside

Downstream raw materials:

(+) trans-chrysanthemum dicarboxylic acid