4-Benzyloxy-benzoic acid (1R,3R,4aR,5S,7aS)-1,3-diethoxy-7-hydroxymethyl-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-5-yl ester

Base Information

• Chemical Name: 4-Benzyloxy-benzoic acid (1R,3R,4aR,5S,7aS)-1,3-diethoxy-7-hydroxymethyl-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-5-yl ester
• CAS No.: 102258-28-6
• Molecular Formula: C₂₇H₃₂O₇
• Molecular Weight: 468.547
• Mol file: 102258-28-6.mol

Synonyms:

Chemical Property of 4-Benzyloxy-benzoic acid (1R,3R,4aR,5S,7aS)-1,3-diethoxy-7-hydroxymethyl-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Benzyloxy-benzoic acid (1R,3R,4aR,5S,7aS)-1,3-diethoxy-7-hydroxymethyl-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-5-yl ester

There total 47 articles about 4-Benzyloxy-benzoic acid (1R,3R,4aR,5S,7aS)-1,3-diethoxy-7-hydroxymethyl-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-5-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:

4-Benzyloxy-benzoic acid (4aR,5S,7aS)-1,3-diethoxy-7-formyl-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-5-yl ester → 4-Benzyloxy-benzoic acid (4aR,5S,7aS)-1,3-diethoxy-7-hydroxymethyl-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-5-yl ester (102258-28-6,102340-09-0,102340-10-3,102340-11-4)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; Yield given;

DOI:10.1039/c39850001719

Reference yield:

(+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol (699-96-7,448922-61-0) → 4-Benzyloxy-benzoic acid (4aR,5S,7aS)-1,3-diethoxy-7-hydroxymethyl-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-5-yl ester (102258-28-6,102340-09-0,102340-10-3,102340-11-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / mCPBA / CH₂Cl₂ / Ambient temperature

2: 81 percent / DBU / CH₂Cl₂ / Ambient temperature

3: 77 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -60 °C

4: 94 percent / Al/Hg, EtOH / tetrahydrofuran / Ambient temperature

5: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -60 °C

7: Et₃N / CH₂Cl₂ / Ambient temperature

8: NaBH₄ / ethanol / 0 °C

With sodium tetrahydroborate; aluminum amalgam; oxalyl dichloride; ethanol; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1039/c39850001719

Reference yield:

(1R,2R,3R,6R,7S,9R)-9-Hydroxymethyl-4-oxa-tricyclo[4.2.1.03,7]nonan-2-ol (102228-27-3,141661-18-9) → 4-Benzyloxy-benzoic acid (4aR,5S,7aS)-1,3-diethoxy-7-hydroxymethyl-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-5-yl ester (102258-28-6,102340-09-0,102340-10-3,102340-11-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / DBU / CH₂Cl₂ / Ambient temperature

2: 77 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -60 °C

3: 94 percent / Al/Hg, EtOH / tetrahydrofuran / Ambient temperature

4: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -60 °C

6: Et₃N / CH₂Cl₂ / Ambient temperature

7: NaBH₄ / ethanol / 0 °C

With sodium tetrahydroborate; aluminum amalgam; oxalyl dichloride; ethanol; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1039/c39850001719

upstream raw materials:

4-(benzyloxy)benzoic acid chloride

(+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol

(1R,2R,3R,6R,7S,9R)-9-Hydroxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol

(1R,2R,3R,6R,7S,9R)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol

Downstream raw materials:

4-Benzyloxy-benzoic acid (1bR,5aS,6R)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

(+/-)-specionin

4-Hydroxy-benzoic acid (1aS,1bS,2S,4R,5aR,6S,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

4-Hydroxy-benzoic acid (1aS,1bS,2R,4S,5aR,6S,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester