Methanesulfonic acid (Z)-(1S,2R,3R,4R,8R,10R)-3,11-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-2,4,8,10-tetramethyl-undec-5-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid (Z)-(1S,2R,3R,4R,8R,10R)-3,11-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-2,4,8,10-tetramethyl-undec-5-enyl ester
• CAS No.: 105676-22-0
• Molecular Formula: C₄₇H₆₄O₆SSi
• Molecular Weight: 785.173

Synonyms:

Chemical Property of Methanesulfonic acid (Z)-(1S,2R,3R,4R,8R,10R)-3,11-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-2,4,8,10-tetramethyl-undec-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (Z)-(1S,2R,3R,4R,8R,10R)-3,11-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-2,4,8,10-tetramethyl-undec-5-enyl ester

There total 36 articles about Methanesulfonic acid (Z)-(1S,2R,3R,4R,8R,10R)-3,11-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-2,4,8,10-tetramethyl-undec-5-enyl 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:

(2S,3R)-3-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1,2-butanediol (105676-47-9) → Methanesulfonic acid (Z)-(1S,2R,3R,4R,8R,10R)-3,11-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-2,4,8,10-tetramethyl-undec-5-enyl ester (105676-22-0)

Guidance literature:

Multi-step reaction with 24 steps

1: 92 percent / pyridine / 0 °C

2: 85 percent / NaOMe / methanol

3: tetrahydrofuran / 0 - 25 °C

4: EDAC*HCl, DMAP / CH₂Cl₂

5: 1) m-CPBA, 2) CaCO₃ / 1) CH₂Cl₂, - 23 deg C, 2) toluene, reflux

6: 91 percent / diethyl ether / -23 °C

7: 90 percent / LiAlH₄ / diethyl ether

8: 96 percent / DMAP, pyridine / CH₂Cl₂

9: Et₃N / CH₂Cl₂

10: LiAlH₄ / diethyl ether

11: aq. AcOH

12: NaIO₄ / methanol; H₂O

13: NaBH₄

14: KH / dimethylformamide

15: MeOH, H⁽¹⁺⁾

16: Et₃N / CH₂Cl₂

17: tetrahydrofuran / 0 °C

18: m-CPBA / CH₂Cl₂

19: 1) n-BuLi / 1) THF, - 78 deg C, 2) THF, -78 deg C

20: Ac₂O, pyridine, DMAP

21: Na/Hg / methanol; tetrahydrofuran

22: MeOH, H⁽¹⁺⁾

23: 95 percent / DMAP, pyridine / CH₂Cl₂

24: Et₃N / CH₂Cl₂

With pyridine; methanol; dmap; sodium tetrahydroborate; sodium periodate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; sodium methylate; acetic anhydride; hydrogen cation; potassium hydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

(4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-4-methyldihydrofuran-2(3H)-one (105676-46-8) → Methanesulfonic acid (Z)-(1S,2R,3R,4R,8R,10R)-3,11-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-2,4,8,10-tetramethyl-undec-5-enyl ester (105676-22-0)

Guidance literature:

Multi-step reaction with 27 steps

1: NaBH₄ / tetrahydrofuran; H₂O

2: H⁽¹⁺⁾ / acetone

3: 62 percent / Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran

4: 92 percent / pyridine / 0 °C

5: 85 percent / NaOMe / methanol

6: tetrahydrofuran / 0 - 25 °C

7: EDAC*HCl, DMAP / CH₂Cl₂

8: 1) m-CPBA, 2) CaCO₃ / 1) CH₂Cl₂, - 23 deg C, 2) toluene, reflux

9: 91 percent / diethyl ether / -23 °C

10: 90 percent / LiAlH₄ / diethyl ether

11: 96 percent / DMAP, pyridine / CH₂Cl₂

12: Et₃N / CH₂Cl₂

13: LiAlH₄ / diethyl ether

14: aq. AcOH

15: NaIO₄ / methanol; H₂O

16: NaBH₄

17: KH / dimethylformamide

18: MeOH, H⁽¹⁺⁾

19: Et₃N / CH₂Cl₂

20: tetrahydrofuran / 0 °C

21: m-CPBA / CH₂Cl₂

22: 1) n-BuLi / 1) THF, - 78 deg C, 2) THF, -78 deg C

23: Ac₂O, pyridine, DMAP

24: Na/Hg / methanol; tetrahydrofuran

25: MeOH, H⁽¹⁺⁾

26: 95 percent / DMAP, pyridine / CH₂Cl₂

27: Et₃N / CH₂Cl₂

With pyridine; methanol; dmap; sodium tetrahydroborate; sodium periodate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; sodium methylate; acetic anhydride; hydrogen cation; potassium hydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;

Reference yield:

1,2-anhydro-3-deoxy-3-C-methyl-4,5-O-isopropylidene-D-arabinitol (105676-49-1) → Methanesulfonic acid (Z)-(1S,2R,3R,4R,8R,10R)-3,11-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-2,4,8,10-tetramethyl-undec-5-enyl ester (105676-22-0)

Guidance literature:

Multi-step reaction with 22 steps

1: tetrahydrofuran / 0 - 25 °C

2: EDAC*HCl, DMAP / CH₂Cl₂

3: 1) m-CPBA, 2) CaCO₃ / 1) CH₂Cl₂, - 23 deg C, 2) toluene, reflux

4: 91 percent / diethyl ether / -23 °C

5: 90 percent / LiAlH₄ / diethyl ether

6: 96 percent / DMAP, pyridine / CH₂Cl₂

7: Et₃N / CH₂Cl₂

8: LiAlH₄ / diethyl ether

9: aq. AcOH

10: NaIO₄ / methanol; H₂O

11: NaBH₄

12: KH / dimethylformamide

13: MeOH, H⁽¹⁺⁾

14: Et₃N / CH₂Cl₂

15: tetrahydrofuran / 0 °C

16: m-CPBA / CH₂Cl₂

17: 1) n-BuLi / 1) THF, - 78 deg C, 2) THF, -78 deg C

18: Ac₂O, pyridine, DMAP

19: Na/Hg / methanol; tetrahydrofuran

20: MeOH, H⁽¹⁺⁾

21: 95 percent / DMAP, pyridine / CH₂Cl₂

22: Et₃N / CH₂Cl₂

With pyridine; methanol; dmap; sodium tetrahydroborate; sodium periodate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; acetic anhydride; hydrogen cation; potassium hydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

methanesulfonyl chloride

(Z)-(2S,3S,4R,5R,9R,11R)-4,12-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-3,5,9,11-tetramethyl-dodec-6-en-2-ol

(2S,3R)-3-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1,2-butanediol

(4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-4-methyldihydrofuran-2(3H)-one

Downstream raw materials:

(R)-2-((Z)-(1R,2R,3R,7R,9R)-2,10-Bis-benzyloxy-1,3,7,9-tetramethyl-dec-4-enyl)-oxirane

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