(5S,6S,7S,8R)-9-Benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one

Base Information

Chemical Name:(5S,6S,7S,8R)-9-Benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one
CAS No.:236427-76-2
Molecular Formula:C₄₁H₇₂O₆Si₃
Molecular Weight:745.276
Hs Code.:

Synonyms:(5S,6S,7S,8R)-9-Benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one

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Chemical Property of (5S,6S,7S,8R)-9-Benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one

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Technology Process of (5S,6S,7S,8R)-9-Benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one

There total 20 articles about (5S,6S,7S,8R)-9-Benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one 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:

: (5R,6S,7S,8R)-4-Benzenesulfonyl-9-benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one

: 236427-76-2
(5S,6S,7S,8R)-9-Benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one

Guidance literature:: With aluminum amalgam; water; In tetrahydrofuran; for 84h; Yield given; Ambient temperature;
DOI:10.1055/s-1999-2689

Reference yield:

: 4039-82-1
Benzyl propargyl ether

: 236427-76-2
(5S,6S,7S,8R)-9-Benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one

Guidance literature:: Multi-step reaction with 19 steps

1: 88 percent / BuLi / tetrahydrofuran / 0.83 h / -78 - 0 °C

2: 73 percent / LAH / tetrahydrofuran / 7.5 h / -78 - 0 °C

3: 93 percent / L-(+)-DET, TBHP, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH₂Cl₂ / 21 h / -25 °C

4: 94 percent / Ti(O-i-Pr)4 / CH₂Cl₂ / 2 h / Ambient temperature

5: 94 percent / NaOH, H₂O / methanol / 0.75 h / Ambient temperature

6: 76 percent / pyridine / CH₂Cl₂ / 18 h / 0 °C

7: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h / 0 °C

8: 98 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

9: Dess-Martin periodinane / CH₂Cl₂ / 48 h

10: benzene / 21 h / Ambient temperature

11: 99 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

12: 93 percent / D-(-)-DET, TBHP, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH₂Cl₂ / 21 h / -25 °C

13: 96 percent / diethyl ether / 23 h / -30 °C

14: 76 percent / Bu₃P / CH₂Cl₂ / 4 h / Ambient temperature

15: 100 percent / (i-Pr)2NEt, TBAI / 1,2-dichloro-ethane / 6 h / Heating

16: 95 percent / m-CPBA, NaH₂PO₄ / CH₂Cl₂ / 0.42 h / Ambient temperature

17: 1.) BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 15 min

18: Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / Ambient temperature

19: Al(Hg), H₂O / tetrahydrofuran / 84 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; sodium dihydrogenphosphate; aluminum amalgam; lithium aluminium tetrahydride; n-butyllithium; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; tributylphosphine; 4 A molecular sieve; water; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; benzene;
DOI:10.1055/s-1999-2689

Reference yield:

: 80885-30-9,81028-03-7,69152-88-1
(E)-4-(benzyloxy)-2-buten-1-ol

: 236427-76-2
(5S,6S,7S,8R)-9-Benzyloxy-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-6-(2-trimethylsilanyl-ethoxymethoxy)-nonan-3-one

Guidance literature:: Multi-step reaction with 17 steps

1: 93 percent / L-(+)-DET, TBHP, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH₂Cl₂ / 21 h / -25 °C

2: 94 percent / Ti(O-i-Pr)4 / CH₂Cl₂ / 2 h / Ambient temperature

3: 94 percent / NaOH, H₂O / methanol / 0.75 h / Ambient temperature

4: 76 percent / pyridine / CH₂Cl₂ / 18 h / 0 °C

5: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h / 0 °C

6: 98 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

7: Dess-Martin periodinane / CH₂Cl₂ / 48 h

8: benzene / 21 h / Ambient temperature

9: 99 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

10: 93 percent / D-(-)-DET, TBHP, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH₂Cl₂ / 21 h / -25 °C

11: 96 percent / diethyl ether / 23 h / -30 °C

12: 76 percent / Bu₃P / CH₂Cl₂ / 4 h / Ambient temperature

13: 100 percent / (i-Pr)2NEt, TBAI / 1,2-dichloro-ethane / 6 h / Heating

14: 95 percent / m-CPBA, NaH₂PO₄ / CH₂Cl₂ / 0.42 h / Ambient temperature

15: 1.) BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 15 min

16: Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / Ambient temperature

17: Al(Hg), H₂O / tetrahydrofuran / 84 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; sodium dihydrogenphosphate; aluminum amalgam; n-butyllithium; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; tributylphosphine; 4 A molecular sieve; water; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; benzene;
DOI:10.1055/s-1999-2689