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

Base Information

• Chemical Name: β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• CAS No.: 89064-71-1
• Molecular Formula: C₃₅H₃₈O₆
• Molecular Weight: 554.683
• Mol file: 89064-71-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 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: 95.0%

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) → β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (89064-71-1)

Guidance literature:

With lithium borohydride; In tetrahydrofuran;

DOI:10.1002/(SICI)1521-3773(19981231)37:24<3436::AID-ANIE3436>3.0.CO;2-Z

Reference yield: 94.0%

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (133697-34-4,97321-70-5) → β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (89064-71-1)

Guidance literature:

With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/jo00376a088

Reference yield: 43.0%

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (133697-34-4,97321-70-5) → β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (89064-71-1) + 2,6-anhydro-1,3,4,5-tetra-O-benzyl-D-glycero-L-gulo-heptitol (79258-16-5)

Guidance literature:

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

With water; In tetrahydrofuran; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 2h; Overall yield = 31 mg; diastereoselective reaction;

DOI:10.3762/bjoc.15.102

upstream raw materials:

1-O-acetyl-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose

1-O-acetyl-3,4,5,7-tetra-O-benzyl-2-deoxy-2-nitro-α-D-gluco-heptulopyranose

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose

1-(O-p-toluenesulfonyl)-3,4,5,7-tetra-O-benzyl-2,6-anhydroglucoheptitol

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol

Trifluoro-methanesulfonic acid (2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl ester