phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

Base Information

Chemical Name:phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam
CAS No.:904895-06-3
Molecular Formula:C₅₃H₅₇NO₁₂S
Molecular Weight:932.101
Hs Code.:

phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

Synonyms:phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

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Chemical Property of phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

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Technology Process of phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

There total 7 articles about phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam 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: 74.0%

: 872120-66-6
phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

: 167612-35-3
2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

: 904895-06-3
phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

: phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In toluene; at -20 ℃; for 2.5h;
DOI:10.1016/j.carres.2006.03.017

Reference yield: 65.0%

: 872120-66-6
phenyl 5-amino-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

: 127061-08-9
2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride

: 904895-06-3
phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

: phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

Guidance literature:: With zirconocene dichloride; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -80 ℃; for 44h;
DOI:10.1016/j.carres.2006.03.017

Reference yield:

: 872120-65-5
phenyl 4,7-di-O-acetyl-5-amino-9-O-benzylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

: 904895-06-3
phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam

Guidance literature:: Multi-step reaction with 2 steps

1: 74 percent / 4 Angstroem molecular sieves; BH₃*NMe₃; AlCl₃ / tetrahydrofuran / 6 h / 0 - 20 °C

2: 65 percent / 4 Angstroem molecular sieves; Cp₂ZrCl₂; AgOTf / CH₂Cl₂ / 44 h / -80 °C

With aluminium trichloride; zirconocene dichloride; trimethylamine-borane; 4 A molecular sieve; silver trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.carres.2006.03.017