1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol
• CAS No.: 129840-37-5
• Molecular Formula: C₂₆H₃₆O₄Si
• Molecular Weight: 440.655
• Mol file: 129840-37-5.mol

Synonyms:1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol

Chemical Property of 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol

There total 9 articles about 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol 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: 97.0%

6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3) + benzyl bromide (100-39-0) → 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol (129840-37-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 0 ℃; for 0.666667h;

Reference yield: 64.0%

benzyl bromide (100-39-0) + 3,4-di-O-acetyl-1,5-anhydro-6-O-t-butyldimethylsilyl-2-deoxy-D-arabino-hex-1-enitol (136656-49-0,117136-33-1) → 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol (129840-37-5)

Guidance literature:

3,4-di-O-acetyl-1,5-anhydro-6-O-t-butyldimethylsilyl-2-deoxy-D-arabino-hex-1-enitol; With sodium methylate; In methanol;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/acschembio.0c00409

Reference yield: 53.0%

6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3) + benzyl bromide (100-39-0) → 4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-D-glucal + 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol (129840-37-5) + 4-O-benzyl-6-O-tert-butyldimethylsilyl-D-(-)-glucal (137792-62-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -5 - 20 ℃; for 4h;

DOI:10.1016/j.bioorg.2007.07.001

upstream raw materials:

6-O-tert-butyldimethylsilyl-D-glucal

benzyl bromide

t-butyldimethylsiyl triflate

3,6-di-O-benzyl-D-glucal

Downstream raw materials:

ethyl 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside

(1S,3R,4S,5R,6S,7S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxa-bicyclo[4.1.0]heptane-7-carboxylic acid methyl ester