(2S,3R)-2-[(4S,5R,6S)-2,2,5-Trimethyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-pentan-3-ol

Base Information

Chemical Name:(2S,3R)-2-[(4S,5R,6S)-2,2,5-Trimethyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-pentan-3-ol
CAS No.:114826-13-0
Molecular Formula:C₂₁H₃₄O₃S
Molecular Weight:366.565
Hs Code.:

Synonyms:(2S,3R)-2-[(4S,5R,6S)-2,2,5-Trimethyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-pentan-3-ol

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Chemical Property of (2S,3R)-2-[(4S,5R,6S)-2,2,5-Trimethyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-pentan-3-ol

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Technology Process of (2S,3R)-2-[(4S,5R,6S)-2,2,5-Trimethyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-pentan-3-ol

There total 34 articles about (2S,3R)-2-[(4S,5R,6S)-2,2,5-Trimethyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-pentan-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: 95.0%

: 930-69-8
sodium thiophenolate

: 114826-25-4
Methanesulfonic acid (R)-2-[(4R,5S,6S)-6-((1S,2R)-2-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester

: 114826-13-0
(2S,3R)-2-[(4S,5R,6S)-2,2,5-Trimethyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-pentan-3-ol

Guidance literature:: In ethanol; at 0 - 25 ℃; for 5h;
DOI:10.1016/S0040-4039(00)95562-X

Reference yield:

: 104265-72-7
(3R,4S)-4-Benzyloxymethoxy-2-methyl-pent-1-en-3-ol

: 114826-13-0
(2S,3R)-2-[(4S,5R,6S)-2,2,5-Trimethyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-pentan-3-ol

Guidance literature:: Multi-step reaction with 19 steps

1: 50percent NaOH / Bu₄NHSO₄ / benzene / 10 °C

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to 25 deg C

3: diethyl ether / -78 °C

4: CF₃CO₂H / benzene / Heating

6: 1.) BH₃*THF, 2.) H₂O₂, aq OH^(1-) / 1.) THF, -78 deg C to 0 deg C, 2.) 0 deg C to 25 deg C

7: i-Pr₂NEt / CH₂Cl₂ / 0 °C

8: BF₃*Et₂O, EtSH / CH₂Cl₂ / 0 °C

9: PCC, 3 Angstroem molecular sieves / CH₂Cl₂

10: 87 percent / tetrahydrofuran / -78 - 25 °C

11: 1.) LiOH / 1.) aq. THF, 2.) AcOH, THF, 25 deg C, 1 h

12: LiAlH₄ / diethyl ether / 16 h / 25 °C

13: i-Pr₂NEt / CH₂Cl₂ / 2 h / -78 °C

14: PPTS / CH₂Cl₂ / 0.5 h / 25 °C

15: LiEt₃BH / tetrahydrofuran / 0.5 h / Heating

16: 1.) BH₃*THF, 2.) H₂O₂, OH^(1-) / 1.) THF, -78 deg C to 0 deg C, 20 h, 2.) 0 deg C to 25 deg C, 24 h

17: 88 percent / Na / diethyl ether; liquid ammonia / 0.03 h / -33 °C

18: i-Pr₂NEt / CH₂Cl₂ / 1 h / -23 °C

19: ethanol / 0 - 25 °C

With lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; borane-THF; dimethylsulfide; 3 A molecular sieve; boron trifluoride diethyl etherate; hydroxide; dihydrogen peroxide; sodium; pyridinium p-toluenesulfonate; lithium triethylborohydride; ozone; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; trifluoroacetic acid; ethanethiol; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ammonia; benzene;
DOI:10.1016/S0040-4039(00)95561-8

Reference yield:

: 114826-12-9
(2S,3R)-2-[(4S,5S,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentan-3-ol

: 114826-13-0
(2S,3R)-2-[(4S,5R,6S)-2,2,5-Trimethyl-6-((S)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-pentan-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: i-Pr₂NEt / CH₂Cl₂ / 1 h / -23 °C

2: ethanol / 0 - 25 °C

With N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane;
DOI:10.1016/S0040-4039(00)95561-8