Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl ester
• CAS No.: 782474-51-5
• Molecular Formula: C₃₀H₄₀O₆S
• Molecular Weight: 528.71
• Mol file: 782474-51-5.mol

Synonyms:Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl ester

There total 14 articles about Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl 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:

(S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol (166022-29-3) → Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl ester (782474-51-5)

Guidance literature:

Multi-step reaction with 9 steps

1: diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran

2: Oxone / methanol

3: n-BuLi

4: n-BuLi

5: Na(Hg); Na₂HPO₄

6: 94 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O

7: 82 percent / H₂ / PtO₂ / 760 Torr

8: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone

9: 4-(dimethylamino)pyridine

With dmap; Oxone; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; methanesulfonamide; di-isopropyl azodicarboxylate; AD-mix-β; hydrogen; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; platinum(IV) oxide; In tetrahydrofuran; methanol; water; tert-butyl alcohol; 6: Sharpless dihydroxylation;

DOI:10.1002/anie.200351868

Reference yield:

(S)-(-)-2,2-dimethyl-6-methylene-1-[1'-(phenylthio)methyl]cyclohexane (502763-33-9) → Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl ester (782474-51-5)

Guidance literature:

Multi-step reaction with 8 steps

1: Oxone / methanol

2: n-BuLi

3: n-BuLi

4: Na(Hg); Na₂HPO₄

5: 94 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O

6: 82 percent / H₂ / PtO₂ / 760 Torr

7: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone

8: 4-(dimethylamino)pyridine

With dmap; Oxone; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; methanesulfonamide; AD-mix-β; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; platinum(IV) oxide; In methanol; water; tert-butyl alcohol; 5: Sharpless dihydroxylation;

DOI:10.1002/anie.200351868

Reference yield:

(S)-1-[1′-benzenesulfonyl]methyl-2,2-dimehtyl-6-methylenecyclohexane (502763-34-0) → Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl ester (782474-51-5)

Guidance literature:

Multi-step reaction with 7 steps

1: n-BuLi

2: n-BuLi

3: Na(Hg); Na₂HPO₄

4: 94 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O

5: 82 percent / H₂ / PtO₂ / 760 Torr

6: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone

7: 4-(dimethylamino)pyridine

With dmap; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; methanesulfonamide; AD-mix-β; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; platinum(IV) oxide; In water; tert-butyl alcohol; 4: Sharpless dihydroxylation;

DOI:10.1002/anie.200351868

upstream raw materials:

p-toluenesulfonyl chloride

(1S,2S)-1-hydroxymethyl-2-[(2S)-2-(5-methoxy-2,7-dimethyl-2H-chromen-2-yl)ethyl]-3,3-dimethylcyclohexanol

(S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol

(S)-(-)-2,2-dimethyl-6-methylene-1-[1'-(phenylthio)methyl]cyclohexane

Downstream raw materials:

siccanin

Refernces