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

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS No.: 183875-30-1
• Molecular Formula: C₃₈H₄₂O₆S
• Molecular Weight: 626.814

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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

There total 2 articles about 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl 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: 72.0%

pivaloyl chloride (3282-30-2) + phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside (183875-29-8) → 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (183875-30-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 24h; Heating;

DOI:10.1021/ja9608555

Reference yield:

phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside (183875-28-7) → 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (183875-30-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaOMe / methanol; tetrahydrofuran / 25 °C

2: 72 percent / 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 24 h / Heating

With dmap; sodium methylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja9608555

Reference yield: 89.0%

2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (183875-30-1) → 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-2-benzenesulfinyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 0.316667h;

DOI:10.1021/ja9608555

upstream raw materials:

pivaloyl chloride

phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

C₃₉H₄₃N₃O₉S

2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-((2R,3R,4R,5S,6R)-3-azido-5-hydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-4-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-((2R,4aR,6R,7R,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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