Toluene-4-sulfonic acid (2R,8R)-2-hydroxy-8-(tetrahydro-pyran-2-yloxy)-nonyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,8R)-2-hydroxy-8-(tetrahydro-pyran-2-yloxy)-nonyl ester
CAS No.:532929-42-3
Molecular Formula:C₂₁H₃₄O₆S
Molecular Weight:414.563
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,8R)-2-hydroxy-8-(tetrahydro-pyran-2-yloxy)-nonyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,8R)-2-hydroxy-8-(tetrahydro-pyran-2-yloxy)-nonyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,8R)-2-hydroxy-8-(tetrahydro-pyran-2-yloxy)-nonyl ester

There total 10 articles about Toluene-4-sulfonic acid (2R,8R)-2-hydroxy-8-(tetrahydro-pyran-2-yloxy)-nonyl 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: 82.0%

: 98-59-9
p-toluenesulfonyl chloride

: 532929-41-2
(2R,8R)-8-(Tetrahydro-pyran-2-yloxy)-nonane-1,2-diol

: 532929-42-3
Toluene-4-sulfonic acid (2R,8R)-2-hydroxy-8-(tetrahydro-pyran-2-yloxy)-nonyl ester

Guidance literature:: With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1021/ol034338k

Reference yield:

: 103367-38-0
methyl 5(R)-(tetrahydropyranyloxy)-hexanoate

: 532929-42-3
Toluene-4-sulfonic acid (2R,8R)-2-hydroxy-8-(tetrahydro-pyran-2-yloxy)-nonyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: LiAlH₄ / tetrahydrofuran / 0 °C

2: pyridine / 0 °C

3: dimethylsulfoxide / 20 °C

4: i-Bu₂AlH / CH₂Cl₂ / -78 °C

5: 99 percent / NaH / tetrahydrofuran / 0 °C

6: i-Bu₂AlH / CH₂Cl₂ / -78 °C

7: 89 percent / (+)-diethyl tartrate; titanium(IV) isopropoxide; t-butyl hydroperoxide / molecular sieves 4 Angstroem / CH₂Cl₂ / -23 °C

8: 80 percent / i-Bu₂AlH / CH₂Cl₂ / 0 °C

9: 82 percent / Bu₂SnO; triethylamine / CH₂Cl₂ / 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; (+)-Weinsaeure-diethylester; triethylamine; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 5: Wittig reaction / 7: Sharpless epoxidation;
DOI:10.1021/ol034338k

Reference yield:

: 195819-11-5
(E)-(R)-5-(Tetrahydro-pyran-2-yloxy)-hex-2-enoic acid methyl ester

: 532929-42-3
Toluene-4-sulfonic acid (2R,8R)-2-hydroxy-8-(tetrahydro-pyran-2-yloxy)-nonyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: NaBH₄; NiCl₂*6H₂O / methanol / 0 °C

2: LiAlH₄ / tetrahydrofuran / 0 °C

3: pyridine / 0 °C

4: dimethylsulfoxide / 20 °C

5: i-Bu₂AlH / CH₂Cl₂ / -78 °C

6: 99 percent / NaH / tetrahydrofuran / 0 °C

7: i-Bu₂AlH / CH₂Cl₂ / -78 °C

8: 89 percent / (+)-diethyl tartrate; titanium(IV) isopropoxide; t-butyl hydroperoxide / molecular sieves 4 Angstroem / CH₂Cl₂ / -23 °C

9: 80 percent / i-Bu₂AlH / CH₂Cl₂ / 0 °C

10: 82 percent / Bu₂SnO; triethylamine / CH₂Cl₂ / 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; (+)-Weinsaeure-diethylester; triethylamine; nickel dichloride; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 6: Wittig reaction / 8: Sharpless epoxidation;
DOI:10.1021/ol034338k