benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate

Base Information

Chemical Name:benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate
CAS No.:1382799-74-7
Molecular Formula:C₁₆H₂₀N₂O₆S
Molecular Weight:368.411
Hs Code.:

Synonyms:benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate

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Chemical Property of benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate

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Technology Process of benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate

There total 1 articles about benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate 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: 73.0%

: (3aR,5R,6S,7R,7aR)-2-(methylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol

: 501-53-1,94274-21-2
benzyl chloroformate

: 1382799-74-7
benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate

Guidance literature:: With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 96h;

Reference yield: 53.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 1382799-74-7
benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate

: 1382799-76-9
benzyl ((3aR,4aR,8aS,9R,9aR)-9-hydroxy-7-phenyl-3a,4a,5,8a,9,9a-hexahydro[1,3]dioxino[4′,5′:5,6]pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate

Guidance literature:: benzaldehyde dimethyl acetal; benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 50 ℃; under a slight vacuum;

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; Cooling;

Reference yield:

: 1382799-74-7
benzyl ((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate

: 1382799-81-6
benzyl methyl((3aR,4aR,8aS,9aR)-7-phenyl-3a,4a,5,8a,9,9a-hexahydro[1,3]dioxino[4′,5′:5,6]pyrano[3,2-d]thiazol-2-yl)carbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 50 °C / under a slight vacuum

1.2: Cooling

2.1: N,N-dimethyl-formamide / 90 °C

3.1: tri-n-butyl-tin hydride / 1,1'-azobis(1-cyanocyclohexanenitrile) / tetrahydrofuran / 3 h / Reflux

With tri-n-butyl-tin hydride; toluene-4-sulfonic acid; 1,1'-azobis(1-cyanocyclohexanenitrile); In tetrahydrofuran; N,N-dimethyl-formamide;