hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• CAS No.: 852395-47-2
• Molecular Formula: C₃₆H₄₀O₇
• Molecular Weight: 584.709
• Mol file: 852395-47-2.mol

Synonyms:hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Chemical Property of hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

There total 7 articles about hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 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: 92.0%

(3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran (194594-76-8) → hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (852395-47-2)

Guidance literature:

(3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran; With ozone; In methanol; at -78 ℃; for 0.0333333 - 0.05h;

With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h;

With hydrogenchloride; In water;

Reference yield:

tert-butyldimethylsilyloxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (934566-55-9) → hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (852395-47-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / sodium methoxide / methanol / 4 h / 20 °C

2: NaH / dimethylformamide / 24 h / 20 °C

3: 6.3 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja070173p

Reference yield:

C14H30SiO7 → hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (852395-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide / 24 h / 20 °C

2: 6.3 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja070173p

upstream raw materials:

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

tert-butyldimethylsilyloxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

2'-hydroxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

acetobromomannose

Downstream raw materials:

Phosphoric acid (2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 2-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

Phosphoric acid (2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

2-(α-D-mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate