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

Base Information

Chemical Name:O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester
CAS No.:552888-50-3
Molecular Formula:C₃₉H₅₂N₂O₉
Molecular Weight:692.85
Hs Code.:

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

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

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

There total 4 articles about O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-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%

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

: 552888-50-3
O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Guidance literature:: With Raney-Ni T₄/Pt; hydrogen; In ethanol; at 20 ℃; for 48h;
DOI:10.1002/ejoc.200390142

Reference yield:

: 23680-31-1
BOC-O-benzyl-L-serine

: 552888-50-3
O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Guidance literature:: Multi-step reaction with 4 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

4: H₂ / platinized Raney Ni T₄ / ethanol / 48 h / Ambient temperature

With 3 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; palladium hydroxide - carbon; platinized Raney Ni T₄; 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

Reference yield:

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

: 552888-50-3
O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

2: H₂ / platinized Raney Ni T₄ / ethanol / 48 h / Ambient temperature

With 3 A molecular sieve; potassium tert-butylate; hydrogen; platinized Raney Ni T₄; In tetrahydrofuran; ethanol; toluene;
DOI:10.1002/(SICI)1099-0690(199905)1999:5<1167::AID-EJOC1167>3.0.CO;2-2