Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 176107-80-5
• Molecular Formula: C₂₃H₃₂O₈S
• Molecular Weight: 468.568
• Mol file: 176107-80-5.mol

Synonyms:Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester

There total 13 articles about Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl 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: 100.0%

methanesulfonyl chloride (124-63-0) + Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-hydroxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester (176107-79-2) → Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester (176107-80-5)

Guidance literature:

With triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1248/cpb.44.627

Reference yield:

ethyl (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate (135897-92-6) → Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester (176107-80-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 86 percent / imidazole / dimethylformamide / Ambient temperature

2: 94 percent / DIBAH / toluene / -78 °C

3: 88 percent / tBuOOH, (-)DIPT, Ti(O-iPr)4 / CH₂Cl₂ / -25 °C

4: 83 percent / Ti(O-iPr)4 / CH₂Cl₂ / 0 - 20 °C

5: 82 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

6: 71 percent / K₂CO₃, MeOH / Ambient temperature

7: 40 percent / CuI / tetrahydrofuran / Ambient temperature

8: 94 percent / DMAP, pyridine / Ambient temperature

9: 68 percent / HF, pyridine / tetrahydrofuran / Ambient temperature

10: t-BuOOH, (-)-DIPT, Ti(O-iPr)4 / CH₂Cl₂ / -25 °C

11: PPTS / CH₂Cl₂ / Ambient temperature

12: collidine / CH₂Cl₂ / -78 °C

13: 100 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; methanol; tert.-butylhydroperoxide; dmap; copper(l) iodide; (-)-diisopropyl tartrate; hydrogen fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.44.627

Reference yield:

(Δ2,3E,Δ6,7E)-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1,8-diol (117638-13-8) → Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester (176107-80-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 88 percent / tBuOOH, (-)DIPT, Ti(O-iPr)4 / CH₂Cl₂ / -25 °C

2: 83 percent / Ti(O-iPr)4 / CH₂Cl₂ / 0 - 20 °C

3: 82 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

4: 71 percent / K₂CO₃, MeOH / Ambient temperature

5: 40 percent / CuI / tetrahydrofuran / Ambient temperature

6: 94 percent / DMAP, pyridine / Ambient temperature

7: 68 percent / HF, pyridine / tetrahydrofuran / Ambient temperature

8: t-BuOOH, (-)-DIPT, Ti(O-iPr)4 / CH₂Cl₂ / -25 °C

9: PPTS / CH₂Cl₂ / Ambient temperature

10: collidine / CH₂Cl₂ / -78 °C

11: 100 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With pyridine; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; methanol; tert.-butylhydroperoxide; dmap; copper(l) iodide; (-)-diisopropyl tartrate; hydrogen fluoride; pyridinium p-toluenesulfonate; potassium carbonate; D-(-)-diisopropyl tartrate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.44.627

upstream raw materials:

methanesulfonyl chloride

Benzoic acid (2R,3S,6S)-6-((R)-2-acetoxy-1-hydroxy-ethyl)-2-but-3-enyl-2,6-dimethyl-tetrahydro-pyran-3-yl ester

ethyl (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate

(Δ^2,3E,Δ^6,7E)-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1,8-diol

Downstream raw materials:

Benzoic acid (2R,3S,6R,7S)-2-but-3-enyl-6-hydroxy-7-hydroxymethyl-2,6-dimethyl-oxepan-3-yl ester