(2S,4S)-2-Phenyl-4-[(2S,5R)-5-((S)-toluene-4-sulfinylmethyl)-tetrahydro-furan-2-yl]-[1,3]dioxane

Base Information

Chemical Name:(2S,4S)-2-Phenyl-4-[(2S,5R)-5-((S)-toluene-4-sulfinylmethyl)-tetrahydro-furan-2-yl]-[1,3]dioxane
CAS No.:862602-94-6
Molecular Formula:C₂₂H₂₆O₄S
Molecular Weight:386.512
Hs Code.:

Synonyms:(2S,4S)-2-Phenyl-4-[(2S,5R)-5-((S)-toluene-4-sulfinylmethyl)-tetrahydro-furan-2-yl]-[1,3]dioxane

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Chemical Property of (2S,4S)-2-Phenyl-4-[(2S,5R)-5-((S)-toluene-4-sulfinylmethyl)-tetrahydro-furan-2-yl]-[1,3]dioxane

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Technology Process of (2S,4S)-2-Phenyl-4-[(2S,5R)-5-((S)-toluene-4-sulfinylmethyl)-tetrahydro-furan-2-yl]-[1,3]dioxane

There total 9 articles about (2S,4S)-2-Phenyl-4-[(2S,5R)-5-((S)-toluene-4-sulfinylmethyl)-tetrahydro-furan-2-yl]-[1,3]dioxane 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:

: 862602-92-4
(2S,4S)-4-{(S)-3-Iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-2-phenyl-[1,3]dioxane

: 862602-94-6
(2S,4S)-2-Phenyl-4-[(2S,5R)-5-((S)-toluene-4-sulfinylmethyl)-tetrahydro-furan-2-yl]-[1,3]dioxane

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at -20 ℃; for 0.5h;
DOI:10.1021/ja0526867

Reference yield:

: 862603-59-6
(S)-1-((2S,4S)-2-Phenyl-[1,3]dioxan-4-yl)-propane-1,3-diol

: 862602-94-6
(2S,4S)-2-Phenyl-4-[(2S,5R)-5-((S)-toluene-4-sulfinylmethyl)-tetrahydro-furan-2-yl]-[1,3]dioxane

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 12 h / 0 °C

2: N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

3: NaI / acetone / 3 h / Heating

4: n-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

With 4-methyl-morpholine; triethyl borane; tri-n-butyl-tin hydride; triethylamine; sodium iodide; In hexane; dichloromethane; acetone; toluene;
DOI:10.1021/ja0526867

Reference yield:

: 862603-51-8
6-(tert-butyl-diphenyl-silanyloxy)-hex-3-enoic acid methyl ester

: 862602-94-6
(2S,4S)-2-Phenyl-4-[(2S,5R)-5-((S)-toluene-4-sulfinylmethyl)-tetrahydro-furan-2-yl]-[1,3]dioxane

Guidance literature:: Multi-step reaction with 8 steps

1: AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

2: LiAlH₄ / tetrahydrofuran / -78 - 20 °C

3: (+/-)-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

4: Bu₄NF / tetrahydrofuran / 3 h / 20 °C

5: Et₃N / CH₂Cl₂ / 12 h / 0 °C

6: N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

7: NaI / acetone / 3 h / Heating

8: n-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

With 4-methyl-morpholine; AD-mix-α; lithium aluminium tetrahydride; triethyl borane; methanesulfonamide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; sodium iodide; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja0526867