(2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde
• CAS No.: 140397-49-5
• Molecular Formula: C₃₅H₃₆O₆
• Molecular Weight: 552.667
• Mol file: 140397-49-5.mol

Synonyms:(2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde

Chemical Property of (2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde

There total 44 articles about (2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde 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: 94.0%

1,3-Dibenzyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-imidazolidine (791097-00-2) → 2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose (113019-43-5,140397-45-1,140397-46-2,140397-47-3,140397-49-5,91738-17-9)

Guidance literature:

With Dowex-H+ resin; In tetrahydrofuran; water;

DOI:10.1016/j.tetlet.2004.08.034

Reference yield: 89.0%

1,3-Diphenyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-imidazolidine (91738-16-8) → 2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose (113019-43-5,140397-45-1,140397-46-2,140397-47-3,140397-49-5,91738-17-9)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; acetone; for 2h;

Reference yield: 41.0%

1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl cyanide (85422-85-1) → (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-6-carbaldehyde + 2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose (113019-43-5,140397-45-1,140397-46-2,140397-47-3,140397-49-5,91738-17-9)

Guidance literature:

1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl cyanide; With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With water; ammonium chloride; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1016/j.carres.2011.04.019

upstream raw materials:

2,6-Anhydro-3,4,5,7-tetra-O-benzyl-aldehydo-D-glycero-D-ido-heptopyranose

β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

1,3-Diphenyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-imidazolidine

2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole

Downstream raw materials:

methyl 3-(2,3,4,6-O-tetrabenzyl-β-D-glucopyranosyl)propenoate

3,7-Anhydro-4,5,6,8-tetra-O-benzyl-1-desoxy-D-erythro-L-talo-octitol

3,7-Anhydro-4,5,6,8-tetra-O-benzyl-1-desoxy-D-erythro-L-galacto-octitol

(3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-[(Z)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran