(3S,5aR,6R,7R,8R,9aS)-3-[N-(tert-butoxycarbonyl)amino]-6,7-bis(benzyloxy)-8-[(benzyloxy)methyl]octahydropyrano[2,3-b][1,5]oxazepin-4-one

Base Information

• Chemical Name: (3S,5aR,6R,7R,8R,9aS)-3-[N-(tert-butoxycarbonyl)amino]-6,7-bis(benzyloxy)-8-[(benzyloxy)methyl]octahydropyrano[2,3-b][1,5]oxazepin-4-one
• CAS No.: 1356389-36-0
• Molecular Formula: C₃₅H₄₂N₂O₈
• Molecular Weight: 618.727
• Mol file: 1356389-36-0.mol

Synonyms:

Chemical Property of (3S,5aR,6R,7R,8R,9aS)-3-[N-(tert-butoxycarbonyl)amino]-6,7-bis(benzyloxy)-8-[(benzyloxy)methyl]octahydropyrano[2,3-b][1,5]oxazepin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5aR,6R,7R,8R,9aS)-3-[N-(tert-butoxycarbonyl)amino]-6,7-bis(benzyloxy)-8-[(benzyloxy)methyl]octahydropyrano[2,3-b][1,5]oxazepin-4-one

There total 10 articles about (3S,5aR,6R,7R,8R,9aS)-3-[N-(tert-butoxycarbonyl)amino]-6,7-bis(benzyloxy)-8-[(benzyloxy)methyl]octahydropyrano[2,3-b][1,5]oxazepin-4-one 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:

O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine (1356389-35-9) → (3S,5aR,6R,7R,8R,9aS)-3-[N-(tert-butoxycarbonyl)amino]-6,7-bis(benzyloxy)-8-[(benzyloxy)methyl]octahydropyrano[2,3-b][1,5]oxazepin-4-one (1356389-36-0)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h;

DOI:10.1002/ejoc.201101148

Reference yield:

O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine methyl ester → (3S,5aR,6R,7R,8R,9aS)-3-[N-(tert-butoxycarbonyl)amino]-6,7-bis(benzyloxy)-8-[(benzyloxy)methyl]octahydropyrano[2,3-b][1,5]oxazepin-4-one (1356389-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: water; lithium hydroxide / 24 h / 20 °C

2: diphenyl phosphoryl azide; triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C

With diphenyl phosphoryl azide; water; triethylamine; lithium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201101148

Reference yield:

O-[(2-(fluorenyl-9-methoxycarbonyl)amino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl]-N-(tert-butoxycarbonyl)-L-serine (1356389-34-8) → (3S,5aR,6R,7R,8R,9aS)-3-[N-(tert-butoxycarbonyl)amino]-6,7-bis(benzyloxy)-8-[(benzyloxy)methyl]octahydropyrano[2,3-b][1,5]oxazepin-4-one (1356389-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: morpholine / dichloromethane / 24 h / 20 °C

2: diphenyl phosphoryl azide; triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C

With morpholine; diphenyl phosphoryl azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201101148

upstream raw materials:

O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine methyl ester

O-[(2-(fluorenyl-9-methoxycarbonyl)amino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl]-N-(tert-butoxycarbonyl)-L-serine

O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine

O-[(2-(fluorenyl-9-methoxycarbonyl)amino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl]-N-(tert-butoxycarbonyl)-L-serine tert-butyl ester