1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene

Base Information

• Chemical Name: 1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene
• CAS No.: 944727-55-3
• Molecular Formula: C₃₅H₄₃NO₆
• Molecular Weight: 573.73

Synonyms:1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene

Chemical Property of 1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene

Chemical Property:

Purity/Quality:

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Technology Process of 1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene

There total 2 articles about 1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + 1-(2'-amino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene (184155-63-3) → 1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene (944727-55-3)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 16h;

DOI:10.1021/jo0700833

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → 1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene (944727-55-3)

Guidance literature:

Multi-step reaction with 2 steps

2: triethylamine / methanol / 16 h / 20 °C

With triethylamine; In methanol;

Reference yield: 89.6%

1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene (944727-55-3) → (2S,3aR,5R,6R,7S,7aS)-1-(tert-butyloxycarbonyl)-6,7-di-O-benzyl-2-(iodomethyl)-5-[(benzyloxy)methyl]octahydropyrano[3,2-b]pyrrole (944727-56-4)

Guidance literature:

With iodine; In diethyl ether; dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo0700833

upstream raw materials:

di-tert-butyl dicarbonate

1-(2'-amino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

(2S,3aR,5R,6R,7S,7aS)-1-(tert-butyloxycarbonyl)-6,7-di-O-benzyl-2-(iodomethyl)-5-[(benzyloxy)methyl]octahydropyrano[3,2-b]pyrrole

(2S,3aR,5R,6S,7R,7aS)-1-(tert-butyloxycarbonyl)-6,7-di-O-benzyl-N'-methyl-octahydro-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

(2S,3aR,5R,6S,7R,7aS)-6,7-di-O-benzyl-N'-methyl-octahydro-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

(2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

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