Toluene-4-sulfonic acid (S)-2-hydroxy-2-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-2-hydroxy-2-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethyl ester
• CAS No.: 104393-72-8
• Molecular Formula: C₁₇H₂₀O₄S
• Molecular Weight: 320.409

Synonyms:Toluene-4-sulfonic acid (S)-2-hydroxy-2-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethyl ester

Chemical Property of Toluene-4-sulfonic acid (S)-2-hydroxy-2-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (S)-2-hydroxy-2-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethyl ester

There total 3 articles about Toluene-4-sulfonic acid (S)-2-hydroxy-2-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethyl 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:

cis-Bicyclo<3.3.0>octa-2,6-diene (17618-97-2,41527-66-6,104393-61-5,110269-92-6) → Toluene-4-sulfonic acid (S)-2-hydroxy-2-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethyl ester (104393-72-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.25 eq. SnCl₄ / 3.5 h / -78 °C

2: 83 percent / LiAlH₄ / tetrahydrofuran

3: pyridine / CH₂Cl₂ / 18 h / from -79 to -33 deg C

With pyridine; lithium aluminium tetrahydride; tin(IV) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00281a057

Reference yield:

(S)-Hydroxy-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester → Toluene-4-sulfonic acid (S)-2-hydroxy-2-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethyl ester (104393-72-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / LiAlH₄ / tetrahydrofuran

2: pyridine / CH₂Cl₂ / 18 h / from -79 to -33 deg C

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00281a057

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + (S)-(1S,3aS,6aS)-1-(1,3a,6,6a-Tetrahydro-pentalen-1-yl)-ethane-1,2-diol (104393-66-0) → Toluene-4-sulfonic acid (S)-2-hydroxy-2-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethyl ester (104393-72-8)

Guidance literature:

With pyridine; In dichloromethane; for 18h; from -79 to -33 deg C;

DOI:10.1021/ja00281a057

upstream raw materials:

p-toluenesulfonyl chloride

(S)-(1S,3aS,6aS)-1-(1,3a,6,6a-Tetrahydro-pentalen-1-yl)-ethane-1,2-diol

cis-Bicyclo<3.3.0>octa-2,6-diene

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