2,2-Dimethyl-propionic acid 2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl ester
• CAS No.: 250226-85-8
• Molecular Formula: C₄₁H₄₈O₇
• Molecular Weight: 652.828
• Mol file: 250226-85-8.mol

Synonyms:2,2-Dimethyl-propionic acid 2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl ester

There total 3 articles about 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl 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: 100.0%

pivaloyl chloride (3282-30-2) + 2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol (81972-20-5) → 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl ester (250226-85-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/ol990885n

Reference yield:

ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate (82614-10-6) → 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl ester (250226-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2: 100 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

With dmap; diisobutylaluminium hydride; triethylamine; In dichloromethane;

DOI:10.1021/ol990885n

Reference yield:

(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal (96689-97-3,120520-77-6,120520-79-8,120520-80-1,120520-78-7) → 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl ester (250226-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 0.5 h / 0 °C

2: 45.9 g / Et₃N; DMAP / CH₂Cl₂ / 20 °C

With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(02)00045-5

upstream raw materials:

pivaloyl chloride

2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol

ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate

(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal

Downstream raw materials:

(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol

(2S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-dihydro-pyran-3-one

2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester

2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-Tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethanol