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

Base Information

Chemical Name:N-(tert-butoxycarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester
CAS No.:552888-37-6
Molecular Formula:C₃₇H₄₆N₂O₁₁
Molecular Weight:694.779
Hs Code.:

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

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

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

There total 3 articles about N-(tert-butoxycarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine 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: 96.0%

: 60538-19-4,79479-07-5,96099-84-2,113525-91-0
N-(tert-butoxycarbonyl)-l-threonine methyl ester

: 211621-55-5
3,4,6-tri-O-benzyl-2-nitro-D-galactal

: 552888-37-6
N-(tert-butoxycarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester

Guidance literature:: With 3 Angstroem MS; potassium tert-butylate; In tetrahydrofuran; toluene;
DOI:10.1002/ejoc.200390142

Reference yield: 45.0%

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

: 113525-91-0
(2S,3S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-hydroxybutanoate

: 1013026-16-8
O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-threonine methyl ester

: 552888-37-6
N-(tert-butoxycarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester

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:

: 3,4,6-tri-O-benzyl-D-galactal

: 1013026-16-8
O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-threonine methyl ester

: 552888-37-6
N-(tert-butoxycarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: acetic anhydride; nitric acid / 0.08 h / -30 °C / Inert atmosphere

1.2: 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: N,N'-bis[(8a,9S)-65-methoxy-9-cinchonanyl]thiourea / acetonitrile / 16 h / Reflux; Inert atmosphere

With N,N'-bis[(8a,9S)-65-methoxy-9-cinchonanyl]thiourea; nitric acid; acetic anhydride; In acetonitrile;
DOI:10.1021/acs.orglett.6b01962