4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-hydroxy-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-hydroxy-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl ester
• CAS No.: 215876-17-8
• Molecular Formula: C₃₄H₄₁NO₁₀S
• Molecular Weight: 655.766

Synonyms:4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-hydroxy-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl ester

Chemical Property of 4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-hydroxy-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-hydroxy-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl ester

There total 12 articles about 4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-hydroxy-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl 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: 76.0%

4-nitrobenzaldehdye (555-16-8) + (R)-1-Benzenesulfonyl-7-hydroxy-10-(4-methoxy-benzyloxy)-2,2-dimethyl-undecane-3,9-dione → 4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-hydroxy-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl ester (215876-17-8)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ja990860j

Reference yield:

2-Phenylthiomethyl-2-methyl-1-propanol (51916-36-0) → 4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-hydroxy-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl ester (215876-17-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: m-CPBA / CH₂Cl₂ / 0 - 23 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

3.1: CH₂Cl₂; diethyl ether / 0 - 23 °C

4.1: 82 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C / *

5.1: K₂OsO₄(OH₂)2; quinuclidine; aq. K₃Fe(CN)6 / 2-methyl-propan-2-ol

6.1: NaIO₄; aq. NaHCO₃ / 2-methyl-propan-2-ol; tetrahydrofuran

7.1: (-)-DIPCl; Et₃N / CH₂Cl₂ / -78 °C

7.2: 87 percent / -70 °C

8.1: 76 percent / SmI₂ / tetrahydrofuran / 0 °C

With Quinuclidine; potassium osmate(VI); sodium periodate; samarium diiodide; oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; (-)-diisopinocamphenylborane chloride; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol; 1.1: Oxidation / 2.1: Oxidation / 3.1: Grignard reaction / 4.1: Oxidation / 5.1: dihydroxylation / 6.1: diol cleavage / 7.1: chiral boronation / 7.2: Substitution / 8.1: Tischenko reduction;

DOI:10.1021/ja990860j

Reference yield:

3-hydroxy-2,2-dimethylpropyl 4-methylbenzenesulfonate (21651-04-7) → 4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-hydroxy-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl ester (215876-17-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 80 °C

2.1: m-CPBA / CH₂Cl₂ / 0 - 23 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: CH₂Cl₂; diethyl ether / 0 - 23 °C

5.1: 82 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C / *

6.1: K₂OsO₄(OH₂)2; quinuclidine; aq. K₃Fe(CN)6 / 2-methyl-propan-2-ol

7.1: NaIO₄; aq. NaHCO₃ / 2-methyl-propan-2-ol; tetrahydrofuran

8.1: (-)-DIPCl; Et₃N / CH₂Cl₂ / -78 °C

8.2: 87 percent / -70 °C

9.1: 76 percent / SmI₂ / tetrahydrofuran / 0 °C

With Quinuclidine; potassium osmate(VI); sodium periodate; samarium diiodide; oxalyl dichloride; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; (-)-diisopinocamphenylborane chloride; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Substitution / 2.1: Oxidation / 3.1: Oxidation / 4.1: Grignard reaction / 5.1: Oxidation / 6.1: dihydroxylation / 7.1: diol cleavage / 8.1: chiral boronation / 8.2: Substitution / 9.1: Tischenko reduction;

DOI:10.1021/ja990860j

upstream raw materials:

4-nitrobenzaldehdye

2-Phenylthiomethyl-2-methyl-1-propanol

3-hydroxy-2,2-dimethylpropyl 4-methylbenzenesulfonate

2,2-Dimethyl-1,3-propanediol

Downstream raw materials:

4-Nitro-benzoic acid (S)-7-benzenesulfonyl-1-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-6,6-dimethyl-5-oxo-heptyl ester

[1-[6-(2-benzenesulfonyl-1,1-dimethyl-ethyl)-3,4-dihydro-2H-pyran-2-ylmethyl]-2-(4-methoxy-benzyloxy)-propoxy]-tert-butyl-dimethyl-silane

(7S,9R,10R)-1-Benzenesulfonyl-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-10-(4-methoxy-benzyloxy)-2,2-dimethyl-undecan-3-one

[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

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