Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propyl ester
CAS No.:862603-20-1
Molecular Formula:C₂₂H₂₈O₆S
Molecular Weight:420.527
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propyl ester

There total 11 articles about Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propyl 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:

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

: 862603-20-1
Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propyl ester

Guidance literature:: Multi-step reaction with 11 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

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; dichloromethane; water; acetone; 6.1: Pummerer rearrangement;
DOI:10.1021/ja0526867

Reference yield:

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

: 862603-20-1
Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

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

With sodium tetrahydroborate; triethylamine; In ethanol; dichloromethane; water;
DOI:10.1021/ja0526867

Reference yield:

: 862603-18-7
(S)-1-((2S,5R)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-but-3-en-1-ol

: 862603-20-1
Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

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

2: aq. NaIO₄ / ethanol / 1 h / 20 °C

3: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

4: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In ethanol; dichloromethane; water; acetone;
DOI:10.1021/ja0526867