3-O-benzyl-6-O-triisopropylsilyl-D-glucal

Base Information

• Chemical Name: 3-O-benzyl-6-O-triisopropylsilyl-D-glucal
• CAS No.: 356067-93-1
• Molecular Formula: C₂₂H₃₆O₄Si
• Molecular Weight: 392.611
• Mol file: 356067-93-1.mol

Synonyms:3-O-benzyl-6-O-triisopropylsilyl-D-glucal

Chemical Property of 3-O-benzyl-6-O-triisopropylsilyl-D-glucal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-O-benzyl-6-O-triisopropylsilyl-D-glucal

There total 3 articles about 3-O-benzyl-6-O-triisopropylsilyl-D-glucal 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:

D-glucal triacetate (2873-29-2) → 3-O-benzyl-6-O-triisopropylsilyl-D-glucal (356067-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaOMe / methanol

2.1: imidazole

3.1: Bu₂SnO

3.2: tetrabutylammonium iodide

With 1H-imidazole; sodium methylate; di(n-butyl)tin oxide; In methanol;

Reference yield:

D-glucal (13265-84-4) → 3-O-benzyl-6-O-triisopropylsilyl-D-glucal (356067-93-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: imidazole

2.1: Bu₂SnO

2.2: tetrabutylammonium iodide

With 1H-imidazole; di(n-butyl)tin oxide;

Reference yield:

benzyl bromide (100-39-0) + 1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (137915-37-8) → 3-O-benzyl-6-O-triisopropylsilyl-D-glucal (356067-93-1)

Guidance literature:

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose; With di(n-butyl)tin oxide; In toluene;

benzyl bromide; With tetra-(n-butyl)ammonium iodide;

DOI:10.1016/S0040-4039(01)00607-4

upstream raw materials:

benzyl bromide

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

D-glucal

D-glucal triacetate

Downstream raw materials:

methyl (n-pentenyl 2-O-benzoyl-3-O-benzyl-4-O-para-methoxybenzyl-β-D-glucopyranosid)-uronate

(2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl (n-pentenyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosid)-uronate

(2S,3S,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester

Refernces

• 1、 Schell, Peter,Orgueira, Hernan A.,Roehrig, Susanne,Seeberger, Peter H.. "Synthesis and transformations of D-glucuronic and L-iduronic acid glycals". . p. 3811 - 3814. Retrieved 2007/10/03.