ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside

Base Information

• Chemical Name: ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside
• CAS No.: 495378-98-8
• Molecular Formula: C₃₂H₄₂O₅Si
• Molecular Weight: 534.768
• Mol file: 495378-98-8.mol

Synonyms:ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside

Chemical Property of ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside

There total 1 articles about ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside 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: 70.0%

p-methoxybenzyl chloride (824-94-2) + ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-α-D-erythro-hexopyranoside → ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside (495378-98-8)

Guidance literature:

With potassium hydroxide; tetrabutylammomium bromide; In toluene; for 2.33333h;

DOI:10.1016/S0008-6215(02)00139-8

Reference yield: 83.0%

ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside (495378-98-8) → ethyl 2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside (495379-00-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 20h;

DOI:10.1016/S0008-6215(02)00139-8

Reference yield:

ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside (495378-98-8) → ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside (495379-07-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / TBAF / tetrahydrofuran / 20 h

2: 2,6-lutidine / CH₂Cl₂ / 0.17 h / -20 °C

3: 52 percent / Bu₄NHSO₄; BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/S0008-6215(02)00139-8

upstream raw materials:

p-methoxybenzyl chloride

Downstream raw materials:

ethyl 2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside

ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside