(1S,3R,4S,5S)-4-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,3R)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-3-methyl-heptan-3-ol

Base Information

• Chemical Name: (1S,3R,4S,5S)-4-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,3R)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-3-methyl-heptan-3-ol
• CAS No.: 326471-47-0
• Molecular Formula: C₅₅H₈₄O₈Si₃
• Molecular Weight: 957.524

Synonyms:(1S,3R,4S,5S)-4-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,3R)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-3-methyl-heptan-3-ol

Chemical Property of (1S,3R,4S,5S)-4-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,3R)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-3-methyl-heptan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4S,5S)-4-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,3R)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-3-methyl-heptan-3-ol

There total 31 articles about (1S,3R,4S,5S)-4-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,3R)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-3-methyl-heptan-3-ol 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:

4-(tert-butyldiphenylsilyloxy)-1-butyne (88158-68-3) → (1S,3R,4S,5S)-4-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,3R)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-3-methyl-heptan-3-ol (326471-47-0)

Guidance literature:

Multi-step reaction with 30 steps

1: BuLi / tetrahydrofuran / 1.5 h / -78 - 0 °C

2: LAH / tetrahydrofuran / 4.5 h / 0 - 23 °C

3: (-)-DET; Ti(OiPr)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / 13 h / -25 °C

4: 91 percent / Ti(OiPr)4 / toluene / 1 h / 100 °C

5: pyridine; DMAP / CH₂Cl₂ / 3.5 h / 0 - 21 °C

6: NaH; TBAI / tetrahydrofuran / 22.5 h / 0 - 22 °C

7: diethyl ether / 0.5 h / 21 °C

8: Dess-Martin periodinane / CH₂Cl₂ / 1.33 h / 22 °C

9: CeCl₃ / tetrahydrofuran / 0.75 h / -78 °C

10: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 22 °C

11: NaH / 22 h / -78 - 23 °C

12: LAH / diethyl ether / 1 h / -20 °C

13: imidazole / dimethylformamide / 1 h / 23 °C

14: DDQ; H₂O / CH₂Cl₂ / 0.5 h / 23 °C

15: DMAP / CH₂Cl₂ / 9 h / 22 °C

16: IBr / toluene / 0.5 h / -94 °C

17: 88 percent / Bu₃SnH; Et₃B / toluene / 5.67 h / -78 - -40 °C

18: 88 percent / K₂CO₃; MeOH / 1.5 h / 26 °C

19: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

20: aq. TFA / tetrahydrofuran / 1 h / 0 °C

21: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

22: K₂CO₃; MeOH / 0.08 h / 24 °C

23: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 24 °C

24: BuLi / tetrahydrofuran / 1 h / -78 °C

25: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

26: 95 percent / NaH / tetrahydrofuran / 2 h / -78 - -40 °C

27: 91 percent / HCl / methanol; CH₂Cl₂ / 0.08 h / 0 °C

28: NaBH₄; CeCl₃*7H₂O / ethanol / 0.5 h / -12 °C

29: mCPBA; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

30: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; triethyl borane; water; tri-n-butyl-tin hydride; iodine(I) bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; (-)-diethyl tartrate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Sharpless asymmetric epoxidation / 11: Horner-Emmons reaction / 26: Horner-Emmons reaction / 28: Luche reduction;

Reference yield:

5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol (88159-03-9) → (1S,3R,4S,5S)-4-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,3R)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-3-methyl-heptan-3-ol (326471-47-0)

Guidance literature:

Multi-step reaction with 29 steps

1: LAH / tetrahydrofuran / 4.5 h / 0 - 23 °C

2: (-)-DET; Ti(OiPr)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / 13 h / -25 °C

3: 91 percent / Ti(OiPr)4 / toluene / 1 h / 100 °C

4: pyridine; DMAP / CH₂Cl₂ / 3.5 h / 0 - 21 °C

5: NaH; TBAI / tetrahydrofuran / 22.5 h / 0 - 22 °C

6: diethyl ether / 0.5 h / 21 °C

7: Dess-Martin periodinane / CH₂Cl₂ / 1.33 h / 22 °C

8: CeCl₃ / tetrahydrofuran / 0.75 h / -78 °C

9: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 22 °C

10: NaH / 22 h / -78 - 23 °C

11: LAH / diethyl ether / 1 h / -20 °C

12: imidazole / dimethylformamide / 1 h / 23 °C

13: DDQ; H₂O / CH₂Cl₂ / 0.5 h / 23 °C

14: DMAP / CH₂Cl₂ / 9 h / 22 °C

15: IBr / toluene / 0.5 h / -94 °C

16: 88 percent / Bu₃SnH; Et₃B / toluene / 5.67 h / -78 - -40 °C

17: 88 percent / K₂CO₃; MeOH / 1.5 h / 26 °C

18: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

19: aq. TFA / tetrahydrofuran / 1 h / 0 °C

20: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

21: K₂CO₃; MeOH / 0.08 h / 24 °C

22: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 24 °C

23: BuLi / tetrahydrofuran / 1 h / -78 °C

24: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

25: 95 percent / NaH / tetrahydrofuran / 2 h / -78 - -40 °C

26: 91 percent / HCl / methanol; CH₂Cl₂ / 0.08 h / 0 °C

27: NaBH₄; CeCl₃*7H₂O / ethanol / 0.5 h / -12 °C

28: mCPBA; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

29: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; triethyl borane; water; tri-n-butyl-tin hydride; iodine(I) bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; (-)-diethyl tartrate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Sharpless asymmetric epoxidation / 10: Horner-Emmons reaction / 25: Horner-Emmons reaction / 27: Luche reduction;

Reference yield:

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol (127665-77-4) → (1S,3R,4S,5S)-4-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,3R)-3-[2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-3-methyl-heptan-3-ol (326471-47-0)

Guidance literature:

Multi-step reaction with 28 steps

1: (-)-DET; Ti(OiPr)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / 13 h / -25 °C

2: 91 percent / Ti(OiPr)4 / toluene / 1 h / 100 °C

3: pyridine; DMAP / CH₂Cl₂ / 3.5 h / 0 - 21 °C

4: NaH; TBAI / tetrahydrofuran / 22.5 h / 0 - 22 °C

5: diethyl ether / 0.5 h / 21 °C

6: Dess-Martin periodinane / CH₂Cl₂ / 1.33 h / 22 °C

7: CeCl₃ / tetrahydrofuran / 0.75 h / -78 °C

8: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 22 °C

9: NaH / 22 h / -78 - 23 °C

10: LAH / diethyl ether / 1 h / -20 °C

11: imidazole / dimethylformamide / 1 h / 23 °C

12: DDQ; H₂O / CH₂Cl₂ / 0.5 h / 23 °C

13: DMAP / CH₂Cl₂ / 9 h / 22 °C

14: IBr / toluene / 0.5 h / -94 °C

15: 88 percent / Bu₃SnH; Et₃B / toluene / 5.67 h / -78 - -40 °C

16: 88 percent / K₂CO₃; MeOH / 1.5 h / 26 °C

17: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

18: aq. TFA / tetrahydrofuran / 1 h / 0 °C

19: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

20: K₂CO₃; MeOH / 0.08 h / 24 °C

21: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 24 °C

22: BuLi / tetrahydrofuran / 1 h / -78 °C

23: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

24: 95 percent / NaH / tetrahydrofuran / 2 h / -78 - -40 °C

25: 91 percent / HCl / methanol; CH₂Cl₂ / 0.08 h / 0 °C

26: NaBH₄; CeCl₃*7H₂O / ethanol / 0.5 h / -12 °C

27: mCPBA; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

28: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; triethyl borane; water; tri-n-butyl-tin hydride; iodine(I) bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; (-)-diethyl tartrate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Sharpless asymmetric epoxidation / 9: Horner-Emmons reaction / 24: Horner-Emmons reaction / 26: Luche reduction;

upstream raw materials:

4-(tert-butyldiphenylsilyloxy)-1-butyne

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol

5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol

(2R,3R)-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)-2-oxiranyl)methan-1-ol

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