methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

Base Information

Chemical Name:methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate
CAS No.:381716-09-2
Molecular Formula:C₂₅H₃₁N₃O₁₁S
Molecular Weight:581.601
Hs Code.:

Synonyms:methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-β-D-galacto-non-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 (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

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Technology Process of methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

There total 2 articles about methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-β-D-galacto-non-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: 59.0%

: 106-45-6
para-thiocresol

: 330815-92-4
methyl 2,4,7,8,9-penta-O-acetyl-5-azido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonate

: 381716-09-2
methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

: 374573-39-4
methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/ja011382r

Reference yield:

: 1071226-27-1
methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate

: 108-24-7
acetic anhydride

: 381716-09-2
methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

: 374573-39-4
methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Guidance literature:: methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate; With methanesulfonic acid; In methanol; at 60 ℃; for 24h;

With triflic azide; copper(II) sulfate; In methanol; at 20 ℃; for 18h;

acetic anhydride; With pyridine; at 0 - 20 ℃; for 4h; Overall yield = 68 percent;
DOI:10.1002/anie.201909177

Reference yield:

: 381716-09-2
methyl (tolyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

: 100-51-6,185532-71-2
benzyl alcohol

: methyl (benzyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

: 352437-49-1
methyl (benzyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -40 ℃; for 2h; Overall yield = 88 percent; Overall yield = 86 mg; stereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1002/anie.201909177