(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl

Base Information

Chemical Name:(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl
CAS No.:862603-24-5
Molecular Formula:C₂₄H₃₀O₄S
Molecular Weight:414.566
Hs Code.:

Synonyms:(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl

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Chemical Property of (2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl

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Technology Process of (2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl

There total 15 articles about (2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl 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%

: 862603-22-3
(2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan

: (2R,5S)-2-Benzyloxymethyl-5-{(S)-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan

: 862603-24-5
(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl

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

Reference yield:

: (R)-4-Benzyloxymethyl-2-phenyl-[1,3]dioxane

: 862603-24-5
(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl

Guidance literature:: Multi-step reaction with 14 steps

1.1: aq. AcOH

1.2: NaIO₄

2.1: Et₃N

3.1: N-methylmorpholine

4.1: NaI

5.1: 95 percent / N-Bu₃SnH; Et₃B

6.1: trifluoroacetic anhydride; pyridine

6.2: 84 percent / KOAc

7.1: 96 percent / MgBr₂*Et₂O

8.1: aq. OsO₄; 4-methylmorpholine N-oxide / acetone / 1.5 h / 20 °C

9.1: aq. NaIO₄ / ethanol / 1 h / 20 °C

10.1: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

11.1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

12.1: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

13.1: 93 percent / NaI / acetone / 9 h / Heating

14.1: 95 percent / N-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

With 4-methyl-morpholine; pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; triethyl borane; tri-n-butyl-tin hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic anhydride; sodium iodide; magnesium bromide; In ethanol; hexane; dichloromethane; water; acetone; toluene; 6.1: Pummerer rearrangement;
DOI:10.1021/ja0526867

Reference yield:

: (S)-3-((2S,5R)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propionaldehyde

: 862603-24-5
(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl

Guidance literature:: Multi-step reaction with 5 steps

1: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

2: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

3: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

4: 93 percent / NaI / acetone / 9 h / Heating

5: 95 percent / N-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

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