(1R,4R,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decane-6,9-diol

Base Information

• Chemical Name: (1R,4R,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decane-6,9-diol
• CAS No.: 131895-69-7
• Molecular Formula: C₁₆H₂₁NO₅S
• Molecular Weight: 339.412

Synonyms:

Chemical Property of (1R,4R,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decane-6,9-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decane-6,9-diol

There total 26 articles about (1R,4R,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decane-6,9-diol 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:

methyl glyoxylate N-tosylhydrazone (89366-20-1) → (1R,4S,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.03,8]decane-6,9-diol (131895-69-7,132015-15-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 80 percent / toluene / Heating

2: 89 percent / m-chloroperoxybenzoic acid (m-CPBA) / CH₂Cl₂ / Heating

3: 92 percent / benzene; CH₂Cl₂ / Heating

4: TsOH / CH₂Cl₂ / 0 °C

5: DIBAL / CH₂Cl₂ / 0 °C

6: t-BuOK / dimethylsulfoxide

7: (COCl)2, DMSO

8: I₂, H₂O / dimethylsulfoxide

9: 97 percent / Bu₃SnH, azoisobutyronitrile / toluene / Heating

10: DIBAL / CH₂Cl₂

11: (COCl)2, DMSO

12: 81 percent / tetrahydrofuran / -30 °C

13: TsOH / tetrahydrofuran / Heating

With oxalyl dichloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; water; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; benzene;

DOI:10.1039/c39900001412

Reference yield:

methyl glyoxylate N-tosylhydrazone (89366-20-1) → (1R,4R,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.03,8]decane-6,9-diol (131895-69-7,132015-15-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 80 percent / toluene / Heating

2: 89 percent / m-chloroperoxybenzoic acid (m-CPBA) / CH₂Cl₂ / Heating

3: 92 percent / benzene; CH₂Cl₂ / Heating

4: TsOH / CH₂Cl₂ / 0 °C

5: DIBAL / CH₂Cl₂ / 0 °C

6: t-BuOK / dimethylsulfoxide

7: (COCl)2, DMSO

8: I₂, H₂O / dimethylsulfoxide

9: 97 percent / Bu₃SnH, azoisobutyronitrile / toluene / Heating

10: DIBAL / CH₂Cl₂

11: (COCl)2, DMSO

12: 81 percent / tetrahydrofuran / -30 °C

13: TsOH / tetrahydrofuran / Heating

With oxalyl dichloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; water; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; benzene;

DOI:10.1039/c39900001412

Reference yield:

(1S,3S,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester (89357-85-7,132015-11-3) → (1R,4S,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.03,8]decane-6,9-diol (131895-69-7,132015-15-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 89 percent / m-chloroperoxybenzoic acid (m-CPBA) / CH₂Cl₂ / Heating

2: 92 percent / benzene; CH₂Cl₂ / Heating

3: TsOH / CH₂Cl₂ / 0 °C

4: DIBAL / CH₂Cl₂ / 0 °C

5: t-BuOK / dimethylsulfoxide

6: (COCl)2, DMSO

7: I₂, H₂O / dimethylsulfoxide

8: 97 percent / Bu₃SnH, azoisobutyronitrile / toluene / Heating

9: DIBAL / CH₂Cl₂

10: (COCl)2, DMSO

11: 81 percent / tetrahydrofuran / -30 °C

12: TsOH / tetrahydrofuran / Heating

With oxalyl dichloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; water; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; benzene;

DOI:10.1039/c39900001412

upstream raw materials:

(1R,6R,8R,9R)-4-Methyl-9-(tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decan-6-ol

methyl glyoxylate N-tosylhydrazone

(1S,3S,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester

(1S,2S,4R,5S,7S)-6-(Toluene-4-sulfonyl)-3-oxa-6-aza-tricyclo[3.2.2.0^2,4]nonane-7-carboxylic acid methyl ester

Downstream raw materials:

N-tosylactinobolamine methyl acetal

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