octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranoside

Base Information

• Chemical Name: octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranoside
• CAS No.: 760190-19-0
• Molecular Formula: C₂₉H₅₀O₆Si
• Molecular Weight: 522.798

Synonyms:octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranoside

Chemical Property of octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranoside

Chemical Property:

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Technology Process of octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranoside

There total 2 articles about octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranoside 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: 90.0%

octanol (111-87-5) + ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside (760190-17-8) → octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranoside (760190-19-0)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 0.833333h;

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 → octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranoside (760190-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.81 g / pyridine / 4 h / 20 °C

2: 90 percent / TMSOTf; N-iodosuccinimide / CH₂Cl₂ / 0.83 h / -20 °C

With pyridine; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/j.carres.2004.06.006

Reference yield: 84.0%

octyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranoside (760190-19-0) → octyl 4-O-acetyl-2-O-benzyl-β-L-fucopyranoside (760190-13-4)

Guidance literature:

With pyridine hydrogenfluoride; In pyridine; at 0 - 20 ℃;

DOI:10.1016/j.carres.2004.06.006

upstream raw materials:

octanol

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

Downstream raw materials:

octyl 4-O-acetyl-2-O-benzyl-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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