Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester

Base Information

Chemical Name:Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester
CAS No.:308240-92-8
Molecular Formula:C₂₇H₄₅NO₆S₂Si
Molecular Weight:571.875
Hs Code.:

Synonyms:Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester

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Chemical Property of Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester

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Technology Process of Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester

There total 11 articles about Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-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:

: 124-63-0
methanesulfonyl chloride

(R)-2-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propan-1-ol: 308240-91-7
(R)-2-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propan-1-ol

: 308240-92-8
Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

: 276870-05-4
(3S)-3-hydroxy-4-(triisopropylsilyloxy)butyric acid methyl ester

: 308240-92-8
Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 76 percent / CSA / CH₂Cl₂ / 72 h / 20 °C

2: 90 percent / LiOH / tetrahydrofuran; H₂O / 12 h / 20 °C

3: Et₃N / 20 °C

4: NH₄OH / 0.5 h / 20 °C

5: 99 percent / Lawesson's reagent / tetrahydrofuran / 0.5 h / 20 °C

6: 2,6-lutidene / CH₂Cl₂ / 12 h / 20 °C

7: (CF₃CO)2O; pyridine / CH₂Cl₂ / 0.5 h / -30 °C

8: 92 percent / AcOH / tetrahydrofuran; H₂O / 12 h / 20 °C

9: Et₃N / CH₂Cl₂ / 1 h / 0 °C

With Lawessons reagent; pyridine; 2,6-dimethylpyridine; lithium hydroxide; ammonium hydroxide; camphor-10-sulfonic acid; acetic acid; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; 1: Alkylation / 2: Hydrolysis / 3: Acylation / 4: amidation / 5: Substitution / 6: Cyclization / 7: Dehydration / 8: Elimination / 9: mesylation;
DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

: 308240-90-6
(+)-(S)-4-tert-Butyldimethylsilyloxy-3-methyl-2-butanone

: 308240-92-8
Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiHMDS / -78 °C

1.2: 86 percent / TMSCl; Br₂

2.1: 2,6-lutidene / CH₂Cl₂ / 12 h / 20 °C

3.1: (CF₃CO)2O; pyridine / CH₂Cl₂ / 0.5 h / -30 °C

4.1: 92 percent / AcOH / tetrahydrofuran; H₂O / 12 h / 20 °C

5.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 2,6-dimethylpyridine; acetic acid; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; 1.1: deprotonation / 1.2: Bromination / 2.1: Cyclization / 3.1: Dehydration / 4.1: Elimination / 5.1: mesylation;
DOI:10.1016/S0040-4039(00)01241-7