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

Base Information

• Chemical Name: O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine methyl ester
• CAS No.: 1013026-14-6
• Molecular Formula: C₃₆H₄₄N₂O₁₁
• Molecular Weight: 680.752

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

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

Chemical Property:

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

There total 4 articles about O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine methyl ester 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: 91.0%

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) + 3,4,6-tri-O-benzyl-2-nitro-D-galactal (211621-55-5) → O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine methyl ester (1013026-14-6)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 24h; optical yield given as %de; stereoselective reaction; Molecular sieve;

DOI:10.1021/jo900609s

Reference yield: 61.0%

2-deoxy-2-nitro-3,4,6-tri-O-benzyl-D-galactal + N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) → O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine methyl ester (1013026-14-6) + O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine methyl ester (1013026-18-0)

Guidance literature:

With N,N'-bis[(8a,9S)-65-methoxy-9-cinchonanyl]thiourea; In acetonitrile; for 16h; diastereoselective reaction; Reflux; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01962

Reference yield: 60.0%

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) + 3,4,6-tri-O-benzyl-2-nitro-D-galactal (211621-55-5) → O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine methyl ester (1013026-14-6) + O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine methyl ester (1013026-18-0)

Guidance literature:

N-tert-butyloxycarbonyl-L-serine methyl ester; 3,4,6-tri-O-benzyl-2-nitro-D-galactal; In toluene; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

With potassium tert-butylate; In tetrahydrofuran; toluene; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201101148

upstream raw materials:

N-tert-butyloxycarbonyl-L-serine methyl ester

3,4,6-tri-O-benzyl-2-nitro-D-galactal

Downstream raw materials:

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

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