1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-arabino-hex-1-enitol
• CAS No.: 1092103-68-8
• Molecular Formula: C₃₅H₃₆O₅
• Molecular Weight: 536.668
• Mol file: 1092103-68-8.mol

Synonyms:1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-arabino-hex-1-enitol

Chemical Property of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-arabino-hex-1-enitol

There total 1 articles about 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-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: 70.0%

benzyl chloride (100-44-7) + 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol (153547-53-6) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-arabino-hex-1-enitol (1092103-68-8)

Guidance literature:

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol; With sodium hydride; In N,N-dimethyl-formamide; paraffin oil; at 0 ℃; for 0.0833333h;

benzyl chloride; In N,N-dimethyl-formamide; paraffin oil; at 20 ℃; for 4h;

DOI:10.1002/ejoc.200800453

Reference yield: 72.0%

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-arabino-hex-1-enitol (1092103-68-8) → benzyl 3,4,6-tri-Obenzyl-2-deoxy-2-C-methylene-α-D-arabino-hexopyranoside

Guidance literature:

With indium(III) chloride; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/ejoc.200800453

Reference yield: 62.0%

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-arabino-hex-1-enitol (1092103-68-8) → (2R,3S)-3-(benzyloxy)-2,5-bis(benzyloxymethyl)-2H-pyran-4(3H)-one + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde (136982-88-2)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bis-[(trifluoroacetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃; for 0.5h; regiospecific reaction; Inert atmosphere;

DOI:10.1021/acs.joc.8b01191

upstream raw materials:

benzyl chloride

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol

Downstream raw materials:

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde