2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester
CAS No.:615250-66-3
Molecular Formula:C₂₅H₃₉NO₉S
Molecular Weight:529.652
Hs Code.:

2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester

There total 4 articles about 2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl 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:

: Acetic acid (2R,3S,4R)-6-acetoxy-4-dimethylamino-2-methyl-tetrahydro-pyran-3-yl ester

: 615250-59-4
2,2-Dimethyl-propionic acid (S)-3-hydroxy-2-(toluene-4-sulfonyloxy)-propyl ester

: 615250-66-3
2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester

: 615250-63-0
2,2-Dimethyl-propionic acid (S)-3-((2S,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester

Guidance literature:: With molecular sieve; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/S0960-894X(03)00659-0

Reference yield:

: 3282-30-2
pivaloyl chloride

: 615250-66-3
2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 7 h / 35 °C

2: 72 percent / DMAP; pyridine / 14 h / 60 °C

3: 72 percent / HCl / methanol / 12 h / 40 °C

4: TMSOTf; molecular sieves / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; hydrogenchloride; dmap; molecular sieve; trimethylsilyl trifluoromethanesulfonate; triethylamine; In methanol; dichloromethane;
DOI:10.1016/S0960-894X(03)00659-0

Reference yield:

: 615250-51-6
2,2-dimethyl-propionic acid 3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-propyl ester

: 615250-66-3
2,2-Dimethyl-propionic acid (S)-3-((2R,4R,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyloxy)-propyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / DMAP; pyridine / 14 h / 60 °C

2: 72 percent / HCl / methanol / 12 h / 40 °C

3: TMSOTf; molecular sieves / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; hydrogenchloride; dmap; molecular sieve; trimethylsilyl trifluoromethanesulfonate; In methanol; dichloromethane;
DOI:10.1016/S0960-894X(03)00659-0