(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran
• CAS No.: 194088-19-2
• Molecular Formula: C₃₇H₃₈O₆
• Molecular Weight: 578.705
• Mol file: 194088-19-2.mol

Synonyms:(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran

Chemical Property of (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran

There total 12 articles about (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran 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: 82.0%

benzyl bromide (100-39-0) + prop-2-ynyl-α-D-glucopyranoside (151168-60-4) → (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran (194088-19-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h; Cooling with ice;

DOI:10.1021/acs.molpharmaceut.0c00917

Reference yield: 79.0%

benzyl bromide (100-39-0) + 1-(2′-propargyl) D-glucose → (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran (194088-19-2) + 1-O-propargyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (194088-16-9)

Guidance literature:

1-(2′-propargyl) D-glucose; With sodium hydride; In N,N-dimethyl-formamide; paraffin oil; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; paraffin oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/b806707d

Reference yield: 51.0%

1-O-propargyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (194088-16-9) → (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran (194088-19-2)

Guidance literature:

With gold(III) tribromide; In acetonitrile; at 70 ℃; for 12h; Inert atmosphere;

DOI:10.1002/ejoc.201100134

upstream raw materials:

benzyl bromide

D-Glucose

1-O-propargyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate

Downstream raw materials:

4'-bromophenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

α-naphthyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

4-(2′-naphthyl) 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

benzyl 2,3,4,6-tetra-O-benzyl-β-D-gluco-pyranoside