2,2-Dimethyl-propionic acid (1R,2R,3R,5R,6R,12S)-12-methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.0^1,5]dodec-2-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (1R,2R,3R,5R,6R,12S)-12-methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.0^1,5]dodec-2-yl ester
• CAS No.: 921203-16-9
• Molecular Formula: C₂₅H₃₇NO₇S₂
• Molecular Weight: 527.703

Synonyms:2,2-Dimethyl-propionic acid (1R,2R,3R,5R,6R,12S)-12-methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.0^1,5]dodec-2-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (1R,2R,3R,5R,6R,12S)-12-methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.0^1,5]dodec-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 2,2-Dimethyl-propionic acid (1R,2R,3R,5R,6R,12S)-12-methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.0^1,5]dodec-2-yl ester

There total 23 articles about 2,2-Dimethyl-propionic acid (1R,2R,3R,5R,6R,12S)-12-methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.0^1,5]dodec-2-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: 81.0%

(1S,2R,3R,5R,6R,12S)-12-Methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.01,5]dodecan-2-ol (921203-14-7) + pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (1R,2R,3R,5R,6R,12S)-12-methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.01,5]dodec-2-yl ester (921203-16-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo061904r

Reference yield:

(3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran (921202-75-7) → 2,2-Dimethyl-propionic acid (1R,2R,3R,5R,6R,12S)-12-methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.01,5]dodec-2-yl ester (921203-16-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: H₂O; 4-methylmorpholine N-oxide; OsO₄ / acetone; 2-methyl-propan-2-ol / 2.5 h / 20 °C

2.1: hydrogen / Pd(OH)2/C / ethyl acetate / 2 h / 20 °C / 760 Torr

3.1: 414 mg / pyridine / -20 °C

4.1: 96 percent / NaN₃ / dimethylformamide / 0.83 h / 90 °C

5.1: hydrogen; pyridine / Pd black / ethanol / 1.5 h / 20 °C / 760 Torr

6.1: triethylamine / acetonitrile / 24 h / 95 °C

7.1: Et₃N / acetonitrile / 4 h / 20 °C

8.1: 85 mg / m-CPBA / CH₂Cl₂ / 1.5 h / 20 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

10.1: NaBH₄ / CH₂Cl₂; methanol / 0.5 h / 20 °C

11.1: NaH / tetrahydrofuran; various solvent(s) / 0.33 h / 20 °C

11.2: 122 mg / tetrahydrofuran; various solvent(s)

12.1: 80 percent / Amberlyst-15 / CH₂Cl₂ / 60 h / 20 °C

13.1: 71 percent / NBS / CH₂Cl₂ / 0.5 h / 0 °C

14.1: 81 percent / DMAP; pyridine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; sodium azide; amberlyst-15; water; hydrogen; sodium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo061904r

Reference yield:

(3aR,5R,6R,6aR)-6-Allyloxy-6-(2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole (921202-70-2) → 2,2-Dimethyl-propionic acid (1R,2R,3R,5R,6R,12S)-12-methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.01,5]dodec-2-yl ester (921203-16-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 93 percent / Grubbs first-generation catalyst / CH₂Cl₂ / 20 °C

2.1: H₂O; 4-methylmorpholine N-oxide; OsO₄ / acetone; 2-methyl-propan-2-ol / 2.5 h / 20 °C

3.1: hydrogen / Pd(OH)2/C / ethyl acetate / 2 h / 20 °C / 760 Torr

4.1: 414 mg / pyridine / -20 °C

5.1: 96 percent / NaN₃ / dimethylformamide / 0.83 h / 90 °C

6.1: hydrogen; pyridine / Pd black / ethanol / 1.5 h / 20 °C / 760 Torr

7.1: triethylamine / acetonitrile / 24 h / 95 °C

8.1: Et₃N / acetonitrile / 4 h / 20 °C

9.1: 85 mg / m-CPBA / CH₂Cl₂ / 1.5 h / 20 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

11.1: NaBH₄ / CH₂Cl₂; methanol / 0.5 h / 20 °C

12.1: NaH / tetrahydrofuran; various solvent(s) / 0.33 h / 20 °C

12.2: 122 mg / tetrahydrofuran; various solvent(s)

13.1: 80 percent / Amberlyst-15 / CH₂Cl₂ / 60 h / 20 °C

14.1: 71 percent / NBS / CH₂Cl₂ / 0.5 h / 0 °C

15.1: 81 percent / DMAP; pyridine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; sodium azide; amberlyst-15; water; hydrogen; sodium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; Grubbs catalyst first generation; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo061904r

upstream raw materials:

(1S,2R,3R,5R,6R,12S)-12-Methoxy-7-(2-methyl-propane-2-sulfonyl)-3-phenylsulfanyl-4,10-dioxa-7-aza-tricyclo[4.3.3.0^1,5]dodecan-2-ol

pivaloyl chloride

C₁₂H₁₉NO₅

(3aR,3bR,7aR,8aR)-3b-(2-Benzyloxy-ethyl)-2,2-dimethyl-3a,5,7a,8a-tetrahydro-3bH-[1,3]dioxolo[4,5]furo[3,2-b]pyran

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