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

Base Information

Chemical Name:O-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-threonine tert-butyl ester
CAS No.:365455-27-2
Molecular Formula:C₃₃H₄₆N₂O₁₁
Molecular Weight:646.735
Hs Code.:

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

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

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

There total 5 articles about O-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-threonine 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: 97.0%

: 365455-29-4
O-(3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-threonine tert-butyl ester

: 365455-27-2
O-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-threonine tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;
DOI:10.1002/1521-3773(20010716)40:14<2654::AID-ANIE2654>3.0.CO;2-L

Reference yield:

: 201800-34-2
3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-galactal

: 365455-27-2
O-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-threonine tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: conc. nitric acid; acetic anhydride / CH₂Cl₂ / 1 h / -30 °C

1.2: 84 percent / triethylamine / CH₂Cl₂ / 0.42 h

2.1: 97 percent / potassium tert-butoxide / toluene; tetrahydrofuran / 2 h

3.1: 97 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 20 °C

With potassium tert-butylate; tetrabutyl ammonium fluoride; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo061670b

Reference yield:

: 30588-71-7
N-(tert-butyloxycarbonyl)-L-threonine tert-butyl ester

: 365455-27-2
O-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-threonine tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / potassium tert-butoxide / toluene; tetrahydrofuran / 2 h

2: 97 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 20 °C

With potassium tert-butylate; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; toluene;
DOI:10.1002/ejoc.200390142 DOI:10.1021/jo061670b