2-(trimethylsiyl)ethyl 4,6-O-(2,3,4,6-tetra-O-benzyl-mannopyranosylidene)-2-O-benzyl-3-O-benzoyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsiyl)ethyl 4,6-O-(2,3,4,6-tetra-O-benzyl-mannopyranosylidene)-2-O-benzyl-3-O-benzoyl-β-D-glucopyranoside
• CAS No.: 319922-37-7
• Molecular Formula: C₅₉H₆₆O₁₂Si
• Molecular Weight: 995.251
• Mol file: 319922-37-7.mol

Synonyms:2-(trimethylsiyl)ethyl 4,6-O-(2,3,4,6-tetra-O-benzyl-mannopyranosylidene)-2-O-benzyl-3-O-benzoyl-β-D-glucopyranoside

Chemical Property of 2-(trimethylsiyl)ethyl 4,6-O-(2,3,4,6-tetra-O-benzyl-mannopyranosylidene)-2-O-benzyl-3-O-benzoyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsiyl)ethyl 4,6-O-(2,3,4,6-tetra-O-benzyl-mannopyranosylidene)-2-O-benzyl-3-O-benzoyl-β-D-glucopyranoside

There total 1 articles about 2-(trimethylsiyl)ethyl 4,6-O-(2,3,4,6-tetra-O-benzyl-mannopyranosylidene)-2-O-benzyl-3-O-benzoyl-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: 67.0%

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone (82598-88-7) + Benzoic acid (2R,3R,4S,5R,6R)-3-benzyloxy-5-hydroxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester → 2-(trimethylsiyl)ethyl 4,6-O-(2,3,4,6-tetra-O-benzyl-mannopyranosylidene)-2-O-benzyl-3-O-benzoyl-β-D-glucopyranoside (319922-37-7)

Guidance literature:

With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate; In toluene; at 20 ℃; for 3h;

DOI:10.1016/S0040-4039(00)01603-8

Reference yield: 56.0%

2-(trimethylsiyl)ethyl 4,6-O-(2,3,4,6-tetra-O-benzyl-mannopyranosylidene)-2-O-benzyl-3-O-benzoyl-β-D-glucopyranoside (319922-37-7) → (2R,3R,4S,5S,6R)-3-Benzyloxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-ol (319922-40-2)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)01603-8

Reference yield:

2-(trimethylsiyl)ethyl 4,6-O-(2,3,4,6-tetra-O-benzyl-mannopyranosylidene)-2-O-benzyl-3-O-benzoyl-β-D-glucopyranoside (319922-37-7) → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-5-benzyloxy-4-hydroxy-6-(2-trimethylsilanyl-ethoxy)-3-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (319922-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether

2: 57 percent / pyridine / 0 °C

With pyridine; lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)01603-8

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone

Downstream raw materials:

(2R,3R,4S,5S,6R)-3-Benzyloxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-ol

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-5-benzyloxy-4-hydroxy-6-(2-trimethylsilanyl-ethoxy)-3-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester