2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde

Base Information

• Chemical Name: 2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde
• CAS No.: 120520-77-6
• Molecular Formula: C₃₆H₃₈O₆
• Molecular Weight: 566.694
• Mol file: 120520-77-6.mol

Synonyms:2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde

Chemical Property of 2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde

There total 29 articles about 2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde 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: 96.0%

1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene (82659-52-7) → 2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde (120520-77-6)

Guidance literature:

1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃; for 2h; Further stages.;

DOI:10.1021/jo702663w

Reference yield: 95.0%

2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde (120520-77-6) → (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal (96689-97-3,120520-77-6,120520-79-8,120520-80-1,120520-78-7)

Guidance literature:

With L-proline; In methanol; for 1h; microwave irradiation;

DOI:10.1021/jo701959b

Reference yield: 94.0%

tetra-O-benzyl-1-<(2'-hydroxy)ethyl>-glucopyranose (124917-60-8) → 2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde (120520-77-6)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 1h;

upstream raw materials:

Acetic acid (E)-3-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl ester

1-(2,3,4,6-O-tetrabenzyl-β-D-glucopyranosyl)-2,3-propanediol

Acetic acid (E)-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl ester

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene

Downstream raw materials:

2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol

((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid

((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1-iodoethane