Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 592500-37-3
• Molecular Formula: C₂₂H₃₀O₇
• Molecular Weight: 406.476
• Mol file: 592500-37-3.mol

Synonyms:Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

There total 5 articles about Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl 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: 83.0%

benzoyl chloride (98-88-4) + Acetic acid (2R,3R,4S,5R,6S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxymethyl-3,5-dimethyl-tetrahydro-pyran-4-yl ester (592500-36-2) → Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester (592500-37-3)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(03)01099-2

Reference yield:

(1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (88424-94-6) → Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester (592500-37-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2.1: O₃ / CH₂Cl₂ / 2 h / -78 °C

2.2: Me₂S / CH₂Cl₂ / 20 °C

3.1: toluene / -78 - 20 °C

3.2: aq. NaOH / diethyl ether / 20 °C

4.1: Hg(OAc)2 / benzene / 5 h / cooling

4.2: Et₃N; DMAP / CH₂Cl₂ / 20 °C

4.3: NaBH₄; O₂ / dimethylformamide / 1.5 h / 20 °C

5.1: 83 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; dmap; mercury(II) diacetate; ozone; triethylamine; In dichloromethane; toluene; benzene;

DOI:10.1016/S0040-4039(03)01099-2

Reference yield:

(2R,3R,4R)-3-Acetoxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol (96094-54-1) → Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester (592500-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: O₃ / CH₂Cl₂ / 2 h / -78 °C

1.2: Me₂S / CH₂Cl₂ / 20 °C

2.1: toluene / -78 - 20 °C

2.2: aq. NaOH / diethyl ether / 20 °C

3.1: Hg(OAc)2 / benzene / 5 h / cooling

3.2: Et₃N; DMAP / CH₂Cl₂ / 20 °C

3.3: NaBH₄; O₂ / dimethylformamide / 1.5 h / 20 °C

4.1: 83 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; mercury(II) diacetate; ozone; In dichloromethane; toluene; benzene;

DOI:10.1016/S0040-4039(03)01099-2

upstream raw materials:

benzoyl chloride

Acetic acid (2R,3R,4S,5R,6S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxymethyl-3,5-dimethyl-tetrahydro-pyran-4-yl ester

(1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

(2R,3R,4R)-3-Acetoxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol

Downstream raw materials:

Benzoic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-(1-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester