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

Base Information

Chemical Name:O-(3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester
CAS No.:365455-28-3
Molecular Formula:C₄₈H₆₂N₂O₁₁Si
Molecular Weight:871.113
Hs Code.:

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

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

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

There total 3 articles about O-(3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-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: 97.0%

: 71630-31-4,7738-22-9
N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

: 365455-25-0
1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol

: 365455-28-3
O-(3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Guidance literature:: With potassium tert-butylate; In toluene;
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

: 365455-28-3
O-(3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 84 percent / triethylamine / CH₂Cl₂ / 0.42 h

2.1: 13 percent / potassium tert-butoxide / toluene; tetrahydrofuran / 1.5 h

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

Reference yield:

: Acetic acid (3R,4R,5R,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-nitro-tetrahydro-pyran-2-yl ester

: 365455-28-3
O-(3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 27 g / Et₃N / CH₂Cl₂ / 0.33 h

2: 97 percent / KOBu-t / toluene

With potassium tert-butylate; triethylamine; In dichloromethane; toluene;
DOI:10.1002/1521-3773(20010716)40:14<2654::AID-ANIE2654>3.0.CO;2-L