methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside

Base Information

• Chemical Name: methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside
• CAS No.: 634909-32-3
• Molecular Formula: C₂₈H₃₈O₆
• Molecular Weight: 470.606
• Mol file: 634909-32-3.mol

Synonyms:methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside

Chemical Property of methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside

There total 7 articles about methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-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: 71.0%

methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside (21317-50-0) + phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-1-thio-L-xylo-hexopyranoside → methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside (634909-32-3)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; acetonitrile; at -78 ℃; for 2h;

DOI:10.1016/j.tetasy.2003.07.023

Reference yield: 34.0%

methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside (21317-50-0) + phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-1-sulfinyl-L-xylo-hexopyranoside (634909-31-2) → methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside (634909-32-3)

Guidance literature:

With trifluoromethylsulfonic anhydride; In dichloromethane;

DOI:10.1016/j.tetasy.2003.07.023

Reference yield:

D-glucal triacetate (2873-29-2) → methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside (634909-32-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: BF₃*OEt₂

1.2: HO^- resin

1.3: 60 percent / H₂ / Pd/C

2.1: 76 percent / pyridinium p-toluenesulfonate / dimethylformamide / 2 h / 80 - 85 °C

3.1: 13.0 g / N-bromosuccinimide; BaCO₃ / CCl₄ / 1 h / Heating

4.1: 96 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / benzene / 20 h / Heating

5.1: 83 percent / NaOH / ethanol; H₂O / 0.25 h / 90 °C

6.1: 71 percent / N-bromosuccinimide / acetonitrile; CH₂Cl₂ / 2 h / -78 °C

With sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; barium carbonate; In tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Ferrier rearrangement;

DOI:10.1016/j.tetasy.2003.07.023

upstream raw materials:

methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside

phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-1-sulfinyl-L-xylo-hexopyranoside

D-glucal triacetate

methyl 4-O-benzoyl-2,3,6-trideoxy-α-D-erythro-hexopyranoside