(E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol

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Chemical Name:(E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol
CAS No.:887768-94-7
Molecular Formula:C₆₁H₈₆O₇Si₂
Molecular Weight:987.521
Hs Code.:
Mol file:887768-94-7.mol

Synonyms:(E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol

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Chemical Property of (E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol Edit

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Technology Process of (E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol

There total 25 articles about (E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-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: 100.0%

: 864712-74-3
(E,4S,5R,6S,7R,8R)-methyl 6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-enoate

: 887768-94-7
(E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 3.5h;
DOI:10.1246/bcsj.79.468

Reference yield:

: 864712-68-5
3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran

: 887768-94-7
(E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol

Guidance literature:: Multi-step reaction with 17 steps

1.1: 97 percent / 9-BBN / tetrahydrofuran / 16 h / 20 °C

2.1: 1.40 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 2.37 g / n-BuLi / tetrahydrofuran; hexane / 13 h / 20 °C

4.1: 2.38 g / H₂ / Pd-C / ethanol / 4 h

5.1: Et₂O*BF₃ / acetic anhydride / 0.5 h / -25 °C

6.1: K₂CO₃ / methanol / 3.5 h / 20 °C

7.1: 2.61 g / NaBH₄ / methanol / 2 h / 20 °C

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

10.1: NaH / tetrahydrofuran

10.2: DIBAL-H / CH₂Cl₂; tetrahydrofuran

11.1: 20 percent / Ti(O-iPr)4; D-(-)-DET; t-butylhydroperoxide / CH₂Cl₂

12.1: 87 percent / CuCN / diethyl ether / 8 h / 0 °C

13.1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / 20 °C

14.1: 64 percent / DIBAL-H / toluene / 8 h / 0 °C

15.1: 98.1 mg / Dess Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

16.1: 101 mg / benzene / 18 h / 100 °C

17.1: 100 percent / LiBH₄ / tetrahydrofuran / 3.5 h / 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; boron trifluoride diethyl etherate; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; acetic anhydride; toluene; benzene; 3.1: Wittig reaction / 9.1: Swern oxidation / 15.1: Dess Martin oxidation / 16.1: Wittig reaction;
DOI:10.1246/bcsj.79.468

Reference yield:

: 887769-09-7
((2R,3R,4R)-3,4-Bis-benzyloxy-5-methoxy-2-methyl-tetrahydro-furan-2-yl)-acetaldehyde

: 887768-94-7
(E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol

Guidance literature:: Multi-step reaction with 15 steps

1.1: 2.37 g / n-BuLi / tetrahydrofuran; hexane / 13 h / 20 °C

2.1: 2.38 g / H₂ / Pd-C / ethanol / 4 h

3.1: Et₂O*BF₃ / acetic anhydride / 0.5 h / -25 °C

4.1: K₂CO₃ / methanol / 3.5 h / 20 °C

5.1: 2.61 g / NaBH₄ / methanol / 2 h / 20 °C

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: NaH / tetrahydrofuran

8.2: DIBAL-H / CH₂Cl₂; tetrahydrofuran

9.1: 20 percent / Ti(O-iPr)4; D-(-)-DET; t-butylhydroperoxide / CH₂Cl₂

10.1: 87 percent / CuCN / diethyl ether / 8 h / 0 °C

11.1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / 20 °C

12.1: 64 percent / DIBAL-H / toluene / 8 h / 0 °C

13.1: 98.1 mg / Dess Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

14.1: 101 mg / benzene / 18 h / 100 °C

15.1: 100 percent / LiBH₄ / tetrahydrofuran / 3.5 h / 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium borohydride; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; boron trifluoride diethyl etherate; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; acetic anhydride; toluene; benzene; 1.1: Wittig reaction / 7.1: Swern oxidation / 13.1: Dess Martin oxidation / 14.1: Wittig reaction;
DOI:10.1246/bcsj.79.468