4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate
• CAS No.: 760190-20-3
• Molecular Formula: C₂₃H₃₄Cl₃NO₆Si
• Molecular Weight: 554.971

Synonyms:4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate

Chemical Property of 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate

Chemical Property:

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Technology Process of 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate

There total 2 articles about 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate 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: 85.0%

trichloroacetonitrile (545-06-2) + ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside (760190-17-8) → 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate (760190-20-3)

Guidance literature:

ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside; With N-Bromosuccinimide; In water; acetone; at 0 ℃; for 0.166667h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 3h;

DOI:10.1016/j.carres.2004.06.006

Reference yield:

(2S,3R,4R,5S,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-ethylsulfanyl-2-methyl-tetrahydro-pyran-3-ol → 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate (760190-20-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1.81 g / pyridine / 4 h / 20 °C

2.1: N-bromosuccinimide / H₂O; acetone / 0.17 h / 0 °C

2.2: 85 percent / DBU / CH₂Cl₂ / 3 h

With pyridine; N-Bromosuccinimide; In water; acetone;

DOI:10.1016/j.carres.2004.06.006

Reference yield: 82.0%

ethyl 2,3-di-O-benzyl-1-thio-β-L-fucopyranoside (138343-57-4) + 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate (760190-20-3) → ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->4)-2,3-di-O-benzyl-1-thio-β-L-fucopyranoside (760190-14-5)

Guidance literature:

With silver trifluoromethanesulfonate; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1016/j.carres.2004.06.006

upstream raw materials:

trichloroacetonitrile

ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside

Downstream raw materials:

ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->4)-2,3-di-O-benzyl-1-thio-β-L-fucopyranoside

octyl 4-O-acetyl-2-O-benzyl-α-L-fucopyranosyl-(1->4)-2,3-di-O-benzyl-α-L-fucopyranosyl-(1->3)-4-O-acetyl-2-O-benzyl-β-L-fucopyranoside

octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-α-L-fucopyranosyl-(1->4)-2,3-di-O-benzyl-α-L-fucopyranosyl-(1->3)-4-O-acetyl-2-O-benzyl-β-L-fucopyranoside

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