(3S,5R,6S,7S,8S)-7-Benzyloxy-3,5-dihydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl ester

Base Information

Chemical Name:(3S,5R,6S,7S,8S)-7-Benzyloxy-3,5-dihydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl ester
CAS No.:351331-57-2
Molecular Formula:C₂₅H₄₀O₅
Molecular Weight:420.59
Hs Code.:

Synonyms:(3S,5R,6S,7S,8S)-7-Benzyloxy-3,5-dihydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,5R,6S,7S,8S)-7-Benzyloxy-3,5-dihydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Hazard Codes:

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Technology Process of (3S,5R,6S,7S,8S)-7-Benzyloxy-3,5-dihydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl ester

There total 16 articles about (3S,5R,6S,7S,8S)-7-Benzyloxy-3,5-dihydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl 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: 89.0%

: 351331-56-1
(3S,5R,6R,7S,8S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl ester

: 351331-57-2
(3S,5R,6S,7S,8S)-7-Benzyloxy-3,5-dihydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.166667h;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#

Reference yield:

: 14642-79-6
benzyloxy-trimethylsilane

: 351331-57-2
(3S,5R,6S,7S,8S)-7-Benzyloxy-3,5-dihydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 16 h / -78 - -50 °C

2.1: BF₃*Et₂O / CH₂Cl₂ / 24 h / -30 °C

3.1: O₃; pyridine / methanol; CH₂Cl₂ / 0.5 h / -78 °C

3.2: 88 percent / dimethylsulfide / pyridine; methanol; CH₂Cl₂ / 16 h / 20 °C

4.1: TiCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

5.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

6.1: 92 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

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

8.1: benzene / 4 h / Heating

9.1: 94 percent / trimethylsilyl chloride / tetrahydrofuran / 4 h / -78 °C

10.1: 91 percent / DIBAL-H / tetrahydrofuran / 3 h / -78 °C

11.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

12.1: NaHMDS / tetrahydrofuran / 0 °C

13.1: DIBAL-H / hexane / 0.5 h / -78 °C

14.1: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

15.1: 81 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

16.1: 89 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; 2,6-dimethylpyridine; chloro-trimethyl-silane; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 7.1: Swern oxidation / 11.1: Swern oxidation / 12.1: Wittig olefination / 14.1: Dess-Martin oxidation;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#

Reference yield:

: 297131-87-4
(2R,3R)-3-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-butyraldehyde

: 351331-57-2
(3S,5R,6S,7S,8S)-7-Benzyloxy-3,5-dihydroxy-4,4,6,8-tetramethyl-undec-10-enoic acid isopropyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: TiCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3: 92 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

4: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: benzene / 4 h / Heating

6: 94 percent / trimethylsilyl chloride / tetrahydrofuran / 4 h / -78 °C

7: 91 percent / DIBAL-H / tetrahydrofuran / 3 h / -78 °C

8: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

9: NaHMDS / tetrahydrofuran / 0 °C

10: DIBAL-H / hexane / 0.5 h / -78 °C

11: Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

12: 81 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

13: 89 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

With 2,6-dimethylpyridine; chloro-trimethyl-silane; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; benzene; 4: Swern oxidation / 8: Swern oxidation / 9: Wittig olefination / 11: Dess-Martin oxidation;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#