(+)-(2R,3R)-2,4,6-trimethyl-benzenesulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-propyl ester

Base Information

Chemical Name:(+)-(2R,3R)-2,4,6-trimethyl-benzenesulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-propyl ester
CAS No.:690223-66-6
Molecular Formula:C₁₆H₁₉N₃O₄S₂
Molecular Weight:381.477
Hs Code.:

Synonyms:(+)-(2R,3R)-2,4,6-trimethyl-benzenesulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-propyl ester

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Chemical Property of (+)-(2R,3R)-2,4,6-trimethyl-benzenesulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-propyl ester

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Technology Process of (+)-(2R,3R)-2,4,6-trimethyl-benzenesulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-propyl ester

There total 5 articles about (+)-(2R,3R)-2,4,6-trimethyl-benzenesulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-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: 80.0%

: 773-64-8
2-mesitylenesulphonyl chloride

: 690223-65-5
(+)-(2R,3R)-3-azido-3-thiophen-2-yl-propane-1,2-diol

: 690223-66-6
(+)-(2R,3R)-2,4,6-trimethyl-benzenesulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-propyl ester

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃; for 24h;
DOI:10.1016/j.tet.2005.04.048

Reference yield:

: 13979-15-2,70326-81-7
ethyl (E)-3-(thiophen-2-yl)acrylate

: 690223-66-6
(+)-(2R,3R)-2,4,6-trimethyl-benzenesulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 66 percent / AD mix-β; (DHQD)2PHAL; MeSO2NH2 / H2O; 2-methyl-propan-2-ol / 15 h / 0 - 15 °C

2: SOCl₂; pyridine / CH₂Cl₂ / 15 h / 0 °C

3: 17 mg / sodium azide / acetonitrile; dimethylformamide / 16 h / 15 °C

4: 90 percent / BH₃*SMe₂; NaBH₄ / tetrahydrofuran / 3 h / 20 °C

5: 80 percent / pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; thionyl chloride; sodium azide; methanesulfonamide; dimethylsulfide borane complex; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/j.tet.2005.04.048

Reference yield:

: 690223-63-3
(-)-(2S,3S)-2,3-dihydroxy-3-thiophen-2-yl-propionic acid ethyl ester

: 690223-66-6
(+)-(2R,3R)-2,4,6-trimethyl-benzenesulfonic acid 3-azido-2-hydroxy-3-thiophen-2-yl-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: SOCl₂; pyridine / CH₂Cl₂ / 15 h / 0 °C

2: 17 mg / sodium azide / acetonitrile; dimethylformamide / 16 h / 15 °C

3: 90 percent / BH₃*SMe₂; NaBH₄ / tetrahydrofuran / 3 h / 20 °C

4: 80 percent / pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; thionyl chloride; sodium azide; dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2005.04.048