(3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate

Base Information

Chemical Name:(3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate
CAS No.:1382800-14-7
Molecular Formula:C₃₅H₄₆N₂O₈SSi
Molecular Weight:682.91
Hs Code.:

(3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate

Synonyms:(3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate

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Chemical Property of (3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate

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Technology Process of (3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate

There total 3 articles about (3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate 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: 78.0%

: 1374769-00-2
tert-butyl allyl((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)carbamate

: 98-88-4
benzoyl chloride

: 1382800-14-7
(3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 0 - 20 ℃;

Reference yield:

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

: 1382800-14-7
(3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / methanol / 2 h / 20 °C

2: dmap; triethylamine / dichloromethane / 40 °C

3: dmap; pyridine / dichloromethane / 0 - 20 °C

With pyridine; dmap; triethylamine; In methanol; dichloromethane;
DOI:10.1021/acs.jmedchem.9b01090

Reference yield:

: 223394-94-3
1,3,4,6-tetra-O-acetyl-2-deoxy-2-<3-(allyl)thioureido>-β-D-glucopyranose

: 1382800-14-7
(3aR,5R,6S,7R,7aR)-2-(allyl(tertbutoxycarbonyl)amino)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl dibenzoate

Guidance literature:: Multi-step reaction with 5 steps

1: trifluoroacetic acid / dichloromethane / 20 °C

2: potassium carbonate / methanol / 20 °C

3: triethylamine / methanol / 2 h / 20 °C

4: dmap; triethylamine / dichloromethane / 40 °C

5: dmap; pyridine / dichloromethane / 0 - 20 °C

With pyridine; dmap; potassium carbonate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/acs.jmedchem.9b01090