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

Base Information

• Chemical Name: O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester
• CAS No.: 225663-00-3
• Molecular Formula: C₃₉H₅₀N₂O₁₁
• Molecular Weight: 722.833
• Mol file: 225663-00-3.mol

Synonyms:O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Chemical Property of O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

There total 5 articles about O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl 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: 84.0%

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (71630-31-4,7738-22-9) + 3,4,6-tri-O-benzyl-2-nitro-D-galactal (211621-55-5) → O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (225663-00-3)

Guidance literature:

3,4,6-tri-O-benzyl-2-nitro-D-galactal; With 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride; caesium carbonate; In tetrachloromethane; hexane; at 20 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester; In tetrachloromethane; hexane; at 20 ℃; for 48h; stereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.7b02543

Reference yield: 13.0%

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (71630-31-4,7738-22-9) + 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-butyloxycarbonyl)-L-serine tert-butyl ester + O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (225663-00-3)

Guidance literature:

With 3 A molecular sieve; potassium tert-butylate; In tetrahydrofuran; toluene; for 2.25h;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1167::AID-EJOC1167>3.0.CO;2-2

Reference yield:

BOC-O-benzyl-L-serine (23680-31-1) → O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (225663-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / BF₃*OEt₂ / cyclohexane; CH₂Cl₂ / 14 h

2: 90 percent / H₂ / Pd(OH)2-C (20 percent Pd) / ethanol; acetic acid / 36 h

3: 80 percent / molecular sieve (3 Angstroem), 1 M t-BuOK / toluene; tetrahydrofuran / 2.25 h

With 3 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; palladium hydroxide - carbon; In tetrahydrofuran; ethanol; dichloromethane; cyclohexane; acetic acid; toluene;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1167::AID-EJOC1167>3.0.CO;2-2

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

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

BOC-O-benzyl-L-serine

N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester

Downstream raw materials:

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

(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

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