(2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde

Base Information

• Chemical Name: (2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde
• CAS No.: 111767-82-9
• Molecular Formula: C₃₄H₃₅O₇P
• Molecular Weight: 586.621
• Mol file: 111767-82-9.mol

Synonyms:(2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde

Chemical Property of (2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde

There total 16 articles about (2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-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: 96.0%

C34H35O6P (124603-99-2) → (2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde (111767-82-9)

Guidance literature:

With dihydrogen peroxide; In diethyl ether; at 25 ℃; for 0.75h;

DOI:10.1021/jo00294a030

Reference yield: 49.0%

carbon monoxide (201230-82-2) + C33H33O6P (111675-18-4) → (2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde (111767-82-9)

Guidance literature:

With <(COD)RhOAc>2; hydrogen; In benzene; at 85 ℃; for 3h; under 35683.2 Torr;

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,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde (111767-82-9)

Guidance literature:

Multi-step reaction with 11 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: 77 percent / 4-pyrrolidinopyridine, DCC / CH₂Cl₂ / 1. 1 h, 25 deg C, 60 deg C, 13 h

10: 8 percent / H₂, <(COD)RhOAc>2 / benzene / 3 h / 85 °C / 32063.2 Torr

11: 96 percent / 1percent H₂O₂ / diethyl ether / 0.75 h / 25 °C

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

DOI:10.1021/jo00294a030

upstream raw materials:

carbon monoxide

C₃₃H₃₃O₆P

C₃₄H₃₅O₆P

4-diphenylphosphanobenzoic acid