Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester
• CAS No.: 162238-25-7
• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.407
• Mol file: 162238-25-7.mol

Synonyms:

Chemical Property of Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

There total 8 articles about Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-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:

2-((3aR,5S,7aS)-2,2,7a-Trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-prop-2-en-1-ol (139618-32-9) → Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester (162238-25-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) catecholborane, Rh(PPh₃)3Cl, 2.) 30percent H₂O₂, 10percent NaOH / 1.) THF

2: 87 percent / lipase PS / various solvent(s)

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂

4: NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol

5: I₂, sat. NaHCO₃ / CH₂Cl₂

6: 93 percent / n-Bu₃SnH, AIBN / benzene / Heating

7: 83 percent / lipase PS, 0.1 M phosphate buffer / acetone / 35 °C

8: Et₃N, DMAP / CH₂Cl₂

With dmap; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; Wilkinson's catalyst; phosphate buffer; 2-methyl-but-2-ene; oxalyl dichloride; Lipase PS; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; In dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4039(94)80031-6

Reference yield:

2-((3aR,5S,7aS)-2,2,7a-Trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-propane-1,3-diol (162084-93-7) → Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester (162238-25-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / lipase PS / various solvent(s)

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂

3: NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol

4: I₂, sat. NaHCO₃ / CH₂Cl₂

5: 93 percent / n-Bu₃SnH, AIBN / benzene / Heating

6: 83 percent / lipase PS, 0.1 M phosphate buffer / acetone / 35 °C

7: Et₃N, DMAP / CH₂Cl₂

With dmap; sodium chlorite; sodium dihydrogenphosphate; phosphate buffer; 2-methyl-but-2-ene; oxalyl dichloride; Lipase PS; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; In dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4039(94)80031-6

Reference yield:

Acetic acid 3-hydroxy-2-((3aR,5S,7aS)-2,2,7a-trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-propyl ester → Benzoic acid (3aS,4aR,7S,7aR,8aR)-2,2,3a-trimethyl-6-oxo-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester (162238-25-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂

2: NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol

3: I₂, sat. NaHCO₃ / CH₂Cl₂

4: 93 percent / n-Bu₃SnH, AIBN / benzene / Heating

5: 83 percent / lipase PS, 0.1 M phosphate buffer / acetone / 35 °C

6: Et₃N, DMAP / CH₂Cl₂

With dmap; sodium chlorite; sodium dihydrogenphosphate; phosphate buffer; 2-methyl-but-2-ene; oxalyl dichloride; Lipase PS; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; In dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4039(94)80031-6

upstream raw materials:

benzoyl chloride

(3aS,4aR,7S,7aR,8aR)-7-Hydroxymethyl-2,2,3a-trimethyl-hexahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-6-one

2-((3aR,5S,7aS)-2,2,7a-Trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-prop-2-en-1-ol

2-((3aR,5S,7aS)-2,2,7a-Trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-propane-1,3-diol

Downstream raw materials:

(+)-paeonilactone