(2R,4aR,6S,7R,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Base Information

• Chemical Name: (2R,4aR,6S,7R,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol
• CAS No.: 370884-51-8
• Molecular Formula: C₂₄H₃₀O₆
• Molecular Weight: 414.499
• Mol file: 370884-51-8.mol

Synonyms:(2R,4aR,6S,7R,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Chemical Property of (2R,4aR,6S,7R,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,7R,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

There total 11 articles about (2R,4aR,6S,7R,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol 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: 53.0%

(2R,4aR,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene (370884-50-7) → (2R,4aR,6R,7S,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol + (2R,4aR,6S,7R,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol (370884-51-8)

Guidance literature:

(2R,4aR,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃;

With sodium hydroxide; dihydrogen peroxide; at 0 ℃;

DOI:10.1016/S0040-4039(01)01205-9

Reference yield:

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester (250226-93-8) → (2R,4aR,6S,7R,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol (370884-51-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 98 percent / H₂ / 5 percent Pd/C / ethyl acetate / 10 h / 20 °C

2.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

2.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

4.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

5.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

6.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.1: 3.0 g / Et₃N; Pd(PPh₃)4 / dimethylformamide / 13 h / 20 °C

8.1: 99 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

9.1: 100 percent / KH / tetrahydrofuran / 1 h / 20 °C

10.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 0 °C

10.2: 53 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; hydrogen; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: Swern oxidation / 5.1: Yamaguchi lactonization;

DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester (116237-17-3) → (2R,4aR,6S,7R,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol (370884-51-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

1.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

3.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

4.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

4.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

5.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.1: 3.0 g / Et₃N; Pd(PPh₃)4 / dimethylformamide / 13 h / 20 °C

7.1: 99 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

8.1: 100 percent / KH / tetrahydrofuran / 1 h / 20 °C

9.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 0 °C

9.2: 53 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Swern oxidation / 4.1: Yamaguchi lactonization;

DOI:10.1016/S0040-4020(02)00039-X

upstream raw materials:

(2R,4aR,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

p-methoxybenzyl chloride

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester

Downstream raw materials:

(2R,4aR,6S,7R,9aS)-7-(4-Methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

(2R,3S,6R,7S)-2-Hydroxymethyl-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-3-ol

1-[(2R,3S,6R,7S)-3-Hydroxy-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-propan-2-one

(2S,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepane-2-carbaldehyde