Methanesulfonic acid 2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethyl ester

Base Information

• Chemical Name: Methanesulfonic acid 2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethyl ester
• CAS No.: 132375-54-3
• Molecular Formula: C₂₄H₃₈O₇SSi
• Molecular Weight: 498.713

Synonyms:

Chemical Property of Methanesulfonic acid 2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid 2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethyl ester

There total 20 articles about Methanesulfonic acid 2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethyl 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:

2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethanol (132375-53-2) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid 2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethyl ester (132375-54-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h;

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Methanesulfonic acid 2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethyl ester (132375-54-3)

Guidance literature:

Multi-step reaction with 19 steps

1: 2) camphersulfonic acid / 1) THF, 80 deg C, 4 h, 2) CH₂Cl₂, 25 deg C, 12 h

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

3: 1) ozone, 2) NaBH₄ / 1) CH₂Cl₂, -78 deg C, 2 h, 2) MeOH, 0 deg C, 2 h

4: 84 percent / I₂, PPh₃, imidazole / acetonitrile / 0.5 h / 25 °C

5: 90 percent / acetonitrile / 48 h / 80 °C

6: 1) n-BuLi / 1) THF, -78 deg C, 1 h, 2) HMPA, -78 deg C - 25 deg C, 18 h

7: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 25 °C

8: 74 percent / AgCO₄, NaHCO₃, 4 Angstroem molecular sieve, silicagel / nitromethane / 4 h / 25 °C

9: 95 percent / Ph₃SnH, AIBN / toluene / 2 h / 110 °C

10: 85 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

11: NEt₃ / CH₂Cl₂ / 1 h / 0 °C

12: DBU / dimethylformamide / 2 h / 145 °C

13: m-chloroperbenzoic acid / tetrahydrofuran; H₂O / 1 h / 0 - 25 °C

14: NaBH₄ / methanol / 1 h / 0 °C

15: 1) NaIO₄, 2) NaBH₄ / 1) EtOH, H₂O, 25 deg C, 1 h, 2) MeOH, 0 deg C, 1 h

16: 82 percent / pyridine / 4 h / -20 - 0 °C

17: 97 percent / imidazole / dimethylformamide / 12 h / 25 °C

18: 98 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

19: NEt₃ / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; camphor-10-sulfonic acid; triphenylstannane; tetrabutyl ammonium fluoride; iodine; silica gel; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; nitromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

2-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-ethanol (132375-34-9) → Methanesulfonic acid 2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethyl ester (132375-54-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 84 percent / I₂, PPh₃, imidazole / acetonitrile / 0.5 h / 25 °C

2: 90 percent / acetonitrile / 48 h / 80 °C

3: 1) n-BuLi / 1) THF, -78 deg C, 1 h, 2) HMPA, -78 deg C - 25 deg C, 18 h

4: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 25 °C

5: 74 percent / AgCO₄, NaHCO₃, 4 Angstroem molecular sieve, silicagel / nitromethane / 4 h / 25 °C

6: 95 percent / Ph₃SnH, AIBN / toluene / 2 h / 110 °C

7: 85 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

8: NEt₃ / CH₂Cl₂ / 1 h / 0 °C

9: DBU / dimethylformamide / 2 h / 145 °C

10: m-chloroperbenzoic acid / tetrahydrofuran; H₂O / 1 h / 0 - 25 °C

11: NaBH₄ / methanol / 1 h / 0 °C

12: 1) NaIO₄, 2) NaBH₄ / 1) EtOH, H₂O, 25 deg C, 1 h, 2) MeOH, 0 deg C, 1 h

13: 82 percent / pyridine / 4 h / -20 - 0 °C

14: 97 percent / imidazole / dimethylformamide / 12 h / 25 °C

15: 98 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

16: NEt₃ / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; triphenylstannane; tetrabutyl ammonium fluoride; iodine; silica gel; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; nitromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

2-[(Z)-(4aR,6S,7R,10aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-6-yl]-ethanol

methanesulfonyl chloride

benzaldehyde dimethyl acetal

2-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-ethanol

Downstream raw materials:

tert-Butyl-[(Z)-(4aR,6S,7R,10aS)-6-(2-iodo-ethyl)-2-phenyl-6,7,10,10a-tetrahydro-4H,4aH-1,3,5-trioxa-benzocycloocten-7-yloxy]-dimethyl-silane

(Z)-(4aR,6S,7R,10aS)-6-{(Z)-3-[(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-3,3-bis-ethylsulfanyl-7-(3-hydroxy-propyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-allyl}-2-phenyl-4,4a,6,7,10,10a-hexahydro-1,3,5-trioxa-benzocycloocten-7-ol

C₄₉H₆₄O₉Si

C₅₄H₇₂O₁₀Si

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