tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)carbamate

Base Information

Chemical Name:tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)carbamate
CAS No.:1374662-06-2
Molecular Formula:C₃₄H₄₉FN₂O₆SSi
Molecular Weight:660.923
Hs Code.:

tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)carbamate

Synonyms:tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)carbamate

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Chemical Property of tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)carbamate

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Technology Process of tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)carbamate

There total 9 articles about tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)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: 25.0%

: 1374662-05-1
tert-butyl (3aR,5R,6S,7R,7aR)-5-((tert-butyldimethylsilyloxy)methyl)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate

: 100-39-0
benzyl bromide

: 1374662-06-2
tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)carbamate

Guidance literature:: tert-butyl (3aR,5R,6S,7R,7aR)-5-((tert-butyldimethylsilyloxy)methyl)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate; With sodium hydride; In N,N-dimethyl-formamide; at 10 ℃; for 0.166667h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; for 0.25h;

Reference yield:

: (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(2-fluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate

: 1374662-06-2
tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)carbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium carbonate; methanol / 20 °C

2.1: triethylamine / methanol / 20 °C

3.1: triethylamine / dmap / dichloromethane / 6 h / 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 10 °C / Inert atmosphere

4.2: 0.25 h

With methanol; sodium hydride; potassium carbonate; triethylamine; dmap; In methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

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

: 1374662-06-2
tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl-(2-fluoroethyl)carbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine / methanol / 20 °C

2.1: triethylamine / dmap / dichloromethane / 6 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 10 °C / Inert atmosphere

3.2: 0.25 h

With sodium hydride; triethylamine; dmap; In methanol; dichloromethane; N,N-dimethyl-formamide;