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

Base Information

• Chemical Name: 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
• CAS No.: 319922-42-4
• Molecular Formula: C₅₇H₇₂O₁₂Si
• Molecular Weight: 977.277
• Mol file: 319922-42-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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: 57.0%

pivaloyl chloride (3282-30-2) + (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) → 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:

With pyridine; at 0 ℃;

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

Reference yield:

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone (82598-88-7) → 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 3 steps

1: 67 percent / TMSOTf; TMSOMe / toluene / 3 h / 20 °C

2: 56 percent / LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether

3: 57 percent / pyridine / 0 °C

With pyridine; lithium aluminium tetrahydride; aluminium trichloride; Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; toluene;

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

Reference yield:

Benzoic acid (2R,3R,4S,5R,6R)-3-benzyloxy-5-hydroxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester → 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 3 steps

1: 67 percent / TMSOTf; TMSOMe / toluene / 3 h / 20 °C

2: 56 percent / LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether

3: 57 percent / pyridine / 0 °C

With pyridine; lithium aluminium tetrahydride; aluminium trichloride; Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; toluene;

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

upstream raw materials:

pivaloyl chloride

(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

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

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