methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl-(1->8)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate

Base Information

Chemical Name:methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl-(1->8)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate
CAS No.:1356479-21-4
Molecular Formula:C₃₁H₃₉N₃O₁₂
Molecular Weight:645.664
Hs Code.:

Synonyms:methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl-(1->8)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl-(1->8)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate

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Technology Process of methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl-(1->8)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate

There total 3 articles about methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl-(1->8)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate 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: 68.0%

: 121260-49-9
C₁₈H₂₆O₁₁

: 1356479-02-1
4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl N-phenyltrifluoroacetimidate

: methyl 4-azido-2,3-di-O-benzyl-4-deoxy-L-arabinopyranosyl-(1->7)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate

: 1356479-21-4
methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl-(1->8)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate

Guidance literature:: C₁₈H₂₆O₁₁; 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl N-phenyltrifluoroacetimidate; In dichloromethane; at -15 ℃; for 2h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -15 - 20 ℃; for 1h; regioselective reaction; Further stages; Mo_.lecular sieve; Inert atmosphere;
DOI:10.1002/ejoc.201101171

Reference yield:

: 4-azido-2,3-di-O-benzyl-4-deoxy-L-arabinopyranose

: 1356479-21-4
methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl-(1->8)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium carbonate / 12 h / 20 °C

2.1: dichloromethane / 2 h / -15 °C / Molecular sieve; Inert atmosphere

2.2: 1 h / -15 - 20 °C / Mo_.lecular sieve; Inert atmosphere

With potassium carbonate; In dichloromethane;
DOI:10.1002/ejoc.201101171

Reference yield:

: 114850-76-9
Methyl (allyl 4,5,7-tri-O-acetyl-8-O-tert-butyldimethylsilyl-3-deoxy-α-D-manno-2-octulopyranosid)onate

: methyl 4-azido-2,3-di-O-benzyl-4-deoxy-L-arabinopyranosyl-(1->7)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate

: 1356479-21-4
methyl 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranosyl-(1->8)-(allyl D-glycero-α-D-talo-oct-2-ulopyranoside)onate

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogen fluoride / acetonitrile / 2 h / 20 °C

2.1: dichloromethane / 2 h / -15 °C / Molecular sieve; Inert atmosphere

2.2: 1 h / -15 - 20 °C / Mo_.lecular sieve; Inert atmosphere

With hydrogen fluoride; In dichloromethane; acetonitrile;
DOI:10.1002/ejoc.201101171