(E)-(4S,5S,6S)-1-Benzyloxymethoxy-8-[1,3]dithian-2-ylidene-4,6-dimethyl-non-2-en-5-ol

Base Information

Chemical Name:(E)-(4S,5S,6S)-1-Benzyloxymethoxy-8-[1,3]dithian-2-ylidene-4,6-dimethyl-non-2-en-5-ol
CAS No.:103563-44-6
Molecular Formula:C₂₃H₃₄O₃S₂
Molecular Weight:422.653
Hs Code.:

Synonyms:(E)-(4S,5S,6S)-1-Benzyloxymethoxy-8-[1,3]dithian-2-ylidene-4,6-dimethyl-non-2-en-5-ol

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Chemical Property of (E)-(4S,5S,6S)-1-Benzyloxymethoxy-8-[1,3]dithian-2-ylidene-4,6-dimethyl-non-2-en-5-ol

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Technology Process of (E)-(4S,5S,6S)-1-Benzyloxymethoxy-8-[1,3]dithian-2-ylidene-4,6-dimethyl-non-2-en-5-ol

There total 16 articles about (E)-(4S,5S,6S)-1-Benzyloxymethoxy-8-[1,3]dithian-2-ylidene-4,6-dimethyl-non-2-en-5-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: 93.0%

: [(E)-(1S,2S)-5-Benzyloxymethoxy-1-((S)-3-[1,3]dithian-2-ylidene-1-methyl-butyl)-2-methyl-pent-3-enyloxy]-tert-butyl-dimethyl-silane

: 103563-44-6
(E)-(4S,5S,6S)-1-Benzyloxymethoxy-8-[1,3]dithian-2-ylidene-4,6-dimethyl-non-2-en-5-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1021/ja00277a028

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 103563-44-6
(E)-(4S,5S,6S)-1-Benzyloxymethoxy-8-[1,3]dithian-2-ylidene-4,6-dimethyl-non-2-en-5-ol

Guidance literature:: Multi-step reaction with 16 steps

1: NaH

2: EtMgBr

3: DIBAL, Br₂

4: 92 percent / n-BuLi / tetrahydrofuran; diethyl ether; hexane / 0.5 h

5: Et₃N / CH₂Cl₂ / 0.33 h / -45 °C

6: DIBAL, Et₃Al / CH₂Cl₂ / 2 h / -78 - -20 °C

7: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

8: CrCl₂ / tetrahydrofuran / 0 °C

9: 92 percent / NaH / hexamethylphosphoric acid triamide / Ambient temperature

10: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

11: 1.) dicyclohexyl borane, 2.) H₂O₂ / 1.) Et₂O, 0 deg C

12: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

13: 96 percent / CeCl₃ / tetrahydrofuran / Ambient temperature

14: 85 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

15: 87 percent / KH / 1,2-dimethoxy-ethane / Ambient temperature

16: 93 percent / TBAF / tetrahydrofuran / Ambient temperature

With 2,6-dimethylpyridine; chromium dichloride; n-butyllithium; cerium(III) chloride; oxalyl dichloride; bis(cyclohexanyl)borane; ethylmagnesium bromide; tetrabutyl ammonium fluoride; dihydrogen peroxide; bromine; triethylaluminum; potassium hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00277a028

Reference yield:

: 96011-46-0
3-(benzyloxymethoxy)prop-1-yne

: 103563-44-6
(E)-(4S,5S,6S)-1-Benzyloxymethoxy-8-[1,3]dithian-2-ylidene-4,6-dimethyl-non-2-en-5-ol

Guidance literature:: Multi-step reaction with 15 steps

1: EtMgBr

2: DIBAL, Br₂

3: 92 percent / n-BuLi / tetrahydrofuran; diethyl ether; hexane / 0.5 h

4: Et₃N / CH₂Cl₂ / 0.33 h / -45 °C

5: DIBAL, Et₃Al / CH₂Cl₂ / 2 h / -78 - -20 °C

6: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

7: CrCl₂ / tetrahydrofuran / 0 °C

8: 92 percent / NaH / hexamethylphosphoric acid triamide / Ambient temperature

9: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

10: 1.) dicyclohexyl borane, 2.) H₂O₂ / 1.) Et₂O, 0 deg C

11: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

12: 96 percent / CeCl₃ / tetrahydrofuran / Ambient temperature

13: 85 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

14: 87 percent / KH / 1,2-dimethoxy-ethane / Ambient temperature

15: 93 percent / TBAF / tetrahydrofuran / Ambient temperature

With 2,6-dimethylpyridine; chromium dichloride; n-butyllithium; cerium(III) chloride; oxalyl dichloride; bis(cyclohexanyl)borane; ethylmagnesium bromide; tetrabutyl ammonium fluoride; dihydrogen peroxide; bromine; triethylaluminum; potassium hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00277a028