(2R,2'S,3'aR,6'S,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde

Base Information

• Chemical Name: (2R,2'S,3'aR,6'S,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde
• CAS No.: 124649-59-8
• Molecular Formula: C₃₄H₃₅O₇P
• Molecular Weight: 586.621
• Mol file: 124649-59-8.mol

Synonyms:(2R,2'S,3'aR,6'S,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde

Chemical Property of (2R,2'S,3'aR,6'S,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,2'S,3'aR,6'S,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde

There total 17 articles about (2R,2'S,3'aR,6'S,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde 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:

3-(diphenylphosphino)benzoic acid (2129-30-8) → (2R,2'S,3'aR,6'S,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde (124649-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / 4-pyrrolidinopyridine, DCC / CH₂Cl₂ / 10 h / 60 °C

2: 1. H₂, <(COD)RhOAc>2 2. t-butyl hydroperoxide / 1. 85 deg C, benzene, 710 psi, 3 h 2. 10 min, toluene

With <(COD)RhOAc>2 2. t-butyl hydroperoxide; hydrogen; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo00294a030

Reference yield:

cis-2-<2-<(4-methoxybenzyl)oxy>-3-cyclohexen-1-yl>-2-propen-1-ol (97826-91-0) → (2R,2'S,3'aR,6'S,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde (124649-59-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 3.4 g / (+)-diethyl L-tartrate, titanium(IV) tert-butoxide, t-BuOOH / CH₂Cl₂ / 5.5 h / -23 °C

2: 1. oxalyl chloride, DMSO 2. NEt₃ / 1. CH₂Cl₂, -55 deg C 2. -55 deg C up to 25 deg C

3: 77 percent / tetrahydrofuran / 0.12 h / -78 °C

4: 1. oxalyl chloride, DMSO 2. NEt₃ / 1. CH₂Cl₂, -55 deg C, 1 h 2. -55 deg C up to 25 deg C

5: 1. LDA / 1. THF, -78 deg C, 50 min 2. -78 deg C, 10 min

6: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzochinone / CH₂Cl₂; H₂O / 1.5 h

7: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h

8: 19 percent / trifluoroacetic acid / CH₂Cl₂ / 0.17 h

9: 88 percent / 4-pyrrolidinopyridine, DCC / CH₂Cl₂ / 10 h / 60 °C

10: 1. H₂, <(COD)RhOAc>2 2. t-butyl hydroperoxide / 1. 85 deg C, benzene, 710 psi, 3 h 2. 10 min, toluene

With titanium(IV) tetrabutoxide; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; <(COD)RhOAc>2 2. t-butyl hydroperoxide; tetrabutyl ammonium fluoride; hydrogen; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00294a030

Reference yield:

2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranecarbaldehyde (97826-92-1) → (2R,2'S,3'aR,6'S,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde (124649-59-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 77 percent / tetrahydrofuran / 0.12 h / -78 °C

2: 1. oxalyl chloride, DMSO 2. NEt₃ / 1. CH₂Cl₂, -55 deg C, 1 h 2. -55 deg C up to 25 deg C

3: 1. LDA / 1. THF, -78 deg C, 50 min 2. -78 deg C, 10 min

4: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzochinone / CH₂Cl₂; H₂O / 1.5 h

5: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h

6: 19 percent / trifluoroacetic acid / CH₂Cl₂ / 0.17 h

7: 88 percent / 4-pyrrolidinopyridine, DCC / CH₂Cl₂ / 10 h / 60 °C

8: 1. H₂, <(COD)RhOAc>2 2. t-butyl hydroperoxide / 1. 85 deg C, benzene, 710 psi, 3 h 2. 10 min, toluene

With oxalyl dichloride; <(COD)RhOAc>2 2. t-butyl hydroperoxide; tetrabutyl ammonium fluoride; hydrogen; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00294a030

upstream raw materials:

carbon monoxide

(2R,2'S,3'aR,7'aR,4''S,5''R)-4''-<<3-(diphenylphosphino)benzoyl>oxy>-5''-methyl-3'a,6',7',7'a,3'',4'',5'',6''-octahydrodispiropyran>

3-(diphenylphosphino)benzoic acid

(2R,2'S,3'aR,7'aR,5''S)-5''-methyl-4-oxo-3'a,6',7',7'a,3'',4'',5'',6''-octahydrodispiropyran>

Downstream raw materials:

(2R,2'S,3'aR,6'R,7'aR,4''S,5''R)-decahydro-4''-<<3-(diphenylphosphinyl)benzoyl>oxy>-5''-methyldispiropyran>-6'-carboxaldehyde

C₃₄H₃₅O₈P

(+)-Phyllanthocin