tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside
• CAS No.: 1040201-58-8
• Molecular Formula: C₅₉H₆₆Cl₃NO₁₁Si
• Molecular Weight: 1099.62
• Mol file: 1040201-58-8.mol

Synonyms:tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside

Chemical Property of tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside

There total 1 articles about tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside 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: 76.0%

C32H36Cl3NO7Si + O-(2,3,4-tri-O-benzyl-α/β-L-fucopyranosyl) trichloroacetimidate → tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside (1040201-58-8)

Guidance literature:

C₃₂H₃₆Cl₃NO₇Si; O-(2,3,4-tri-O-benzyl-α/β-L-fucopyranosyl) trichloroacetimidate; In dichloromethane; at -30 ℃; for 1h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 1h; Further stages; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.joc.7b03117

Reference yield: 86.0%

tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside (1040201-58-8) + methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2→3)-phenyl 2,6-dio-O-acetyl-6-O-benzyl-1-thio-β-D-galactothiopyranoside → tert-butyldiphenylsilyl methyl-5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2→3)-2,6-di-O-acetyl-6-O-benzyl-β-D-galactothiopyranosyl-β-(1→4)[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside

Guidance literature:

tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside; methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2→3)-phenyl 2,6-dio-O-acetyl-6-O-benzyl-1-thio-β-D-galactothiopyranoside; In dichloromethane; at 20 ℃; for 1h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -40 ℃; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.joc.7b03117

Reference yield: 63.0%

C22H26Cl3NO9 + tert-butyldiphenylsilyl [2,3,4-tri-O-benzyl-α-L-fucopyranosyl-α-(1→3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside (1040201-58-8) → C78H88Cl3NO19Si (1040201-61-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; Molecular sieve;

DOI:10.1002/anie.200705762

Downstream raw materials:

C₇₈H₈₈Cl₃NO₁₉Si