Trifluoro-methanesulfonic acid (S)-[(4R,5S)-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (S)-[(4R,5S)-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester
• CAS No.: 914083-38-8
• Molecular Formula: C₂₆H₃₉F₃O₈S
• Molecular Weight: 568.652

Synonyms:

Chemical Property of Trifluoro-methanesulfonic acid (S)-[(4R,5S)-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (S)-[(4R,5S)-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester

There total 16 articles about Trifluoro-methanesulfonic acid (S)-[(4R,5S)-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl 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)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (914083-36-6) + trifluoromethylsulfonic anhydride (358-23-6) → Trifluoro-methanesulfonic acid (S)-[(4R,5S)-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester (914083-38-8)

Guidance literature:

With pyridine; In dichloromethane; at -10 ℃;

DOI:10.1016/j.tetlet.2006.07.107

Reference yield:

(S)-8-Benzyloxy-3-methyl-octanal (914083-14-0) → Trifluoro-methanesulfonic acid (S)-[(4R,5S)-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester (914083-38-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / LiHMDS / tetrahydrofuran / 2 h / -78 °C

2: 90 percent / Ph₃P / benzene / 20 °C

3: AD mix-αMeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

4: CSA / CH₂Cl₂ / 1 h

5: 87 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 0 °C

6: 80 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

7: 85 percent / CSA / CH₂Cl₂ / 20 °C

8: pyridine / CH₂Cl₂ / -10 °C

With pyridine; AD-mix-α; lithium aluminium tetrahydride; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; benzene; 3: Sharpless asymmetric dihydroxylation / 5: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetlet.2006.07.107

Reference yield:

(S)-8-Benzyloxy-3-methyl-octan-1-ol (914083-07-1) → Trifluoro-methanesulfonic acid (S)-[(4R,5S)-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester (914083-38-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / IBX / dimethylsulfoxide; tetrahydrofuran / 3 h / 20 °C

2: 86 percent / LiHMDS / tetrahydrofuran / 2 h / -78 °C

3: 90 percent / Ph₃P / benzene / 20 °C

4: AD mix-αMeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

5: CSA / CH₂Cl₂ / 1 h

6: 87 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 0 °C

7: 80 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

8: 85 percent / CSA / CH₂Cl₂ / 20 °C

9: pyridine / CH₂Cl₂ / -10 °C

With pyridine; AD-mix-α; lithium aluminium tetrahydride; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; triphenylphosphine; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; benzene; 4: Sharpless asymmetric dihydroxylation / 6: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetlet.2006.07.107

upstream raw materials:

(S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

trifluoromethylsulfonic anhydride

(S)-8-Benzyloxy-3-methyl-octanal

(S)-8-Benzyloxy-3-methyl-octan-1-ol

Downstream raw materials:

((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

((S)-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methyl)-carbamic acid tert-butyl ester

((1S,2S)-2,3-Dihydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

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