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

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Chemical Name: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
CAS No.:183875-31-2
Molecular Formula:C₄₄H₅₁N₃O₁₀S
Molecular Weight:813.969
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 78.0%

: 183875-13-0
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

: 183875-31-2
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

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 1h;
DOI:10.1021/ja9608555

Reference yield:

: 3282-30-2
pivaloyl chloride

: 183875-31-2
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

Guidance literature:: Multi-step reaction with 4 steps

1: 72 percent / 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 24 h / Heating

2: 89 percent / MCPBA / CH₂Cl₂ / 0.32 h / -78 °C

3: 1.) Tf₂O, 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) CH₂Cl₂, from -60 to 0 deg C, 70 min

4: 78 percent / TFA / CH₂Cl₂ / 1 h / 25 °C

With dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/ja9608555

Reference yield:

: 171032-74-9
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 183875-31-2
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

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 72 h / 25 °C

2: NaOMe / methanol; tetrahydrofuran / 1 h / 25 °C

3: 89 percent / TsOH*H₂O / dimethylformamide / 24 h / 25 °C

4: 1.) Tf₂O, 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) CH₂Cl₂, from -60 to 0 deg C, 70 min

5: 78 percent / TFA / CH₂Cl₂ / 1 h / 25 °C

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9608555