Ethanone, 1-[1,2,3,4-tetrahydro-2-hydroxy-5-methoxy-8-(phenylmethoxy)-2-naphth alenyl]-, (R)-

Base Information

• Chemical Name: Ethanone, 1-[1,2,3,4-tetrahydro-2-hydroxy-5-methoxy-8-(phenylmethoxy)-2-naphth alenyl]-, (R)-
• CAS No.: 81504-96-3
• Molecular Formula: C20H22O4
• Molecular Weight: 326.392
• Mol file: 81504-96-3.mol

Synonyms:

Chemical Property of Ethanone, 1-[1,2,3,4-tetrahydro-2-hydroxy-5-methoxy-8-(phenylmethoxy)-2-naphth alenyl]-, (R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethanone, 1-[1,2,3,4-tetrahydro-2-hydroxy-5-methoxy-8-(phenylmethoxy)-2-naphth alenyl]-, (R)-

There total 11 articles about Ethanone, 1-[1,2,3,4-tetrahydro-2-hydroxy-5-methoxy-8-(phenylmethoxy)-2-naphth alenyl]-, (R)- 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%

(-)-(2R,1'S)-8-benzyloxy-2-(1'-hydroxyethyl)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol (90744-27-7) → (R)-(-)-2-Acetyl-5-methoxy-8-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-2-ol (81504-96-3)

Guidance literature:

With silver carbonate; In benzene; Heating;

DOI:10.1016/S0040-4039(01)80201-X

Reference yield: 69.0%

(-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione (81504-95-2) → (R)-(-)-2-Acetyl-5-methoxy-8-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-2-ol (81504-96-3)

Guidance literature:

With methyllithium; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1071/CH9841709

Reference yield:

Methyl 5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoate (6395-09-1) → (R)-(-)-2-Acetyl-5-methoxy-8-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-2-ol (81504-96-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) potassium bis(trimethylsilyl)amide, 2.) (-)-(8,8-dimethoxycamphorsulfonyl)oxaziridine / 1.) toluene, THF, -78 deg C, 30 min, 2.) -78 deg C, 5 h

2: 82 percent / BBr₃ / CH₂Cl₂ / 3 h / -78 °C

3: 90 percent / Et₃SiH / trifluoroacetic acid / 16 h / Ambient temperature

4: 1.) NaH, DMSO, 2.) Al/Hg, H₂O / 1.) THF, 0 deg C, 1 h, 2.) THF, 16 h

5: 44 percent / K₂CO₃ / acetone / 16 h / Heating

With triethylsilane; aluminum amalgam; (-)-(8,8-Dimethoxycamphoryl)sulfonyl>oxaziridine; water; boron tribromide; potassium hexamethylsilazane; sodium hydride; potassium carbonate; dimethyl sulfoxide; In dichloromethane; acetone; trifluoroacetic acid;

DOI:10.1021/jo00084a042

upstream raw materials:

methyllithium

(-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione

(-)-(2R,1'S)-8-benzyloxy-2-(1'-hydroxyethyl)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

Methyl 5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoate

Downstream raw materials:

(-)-(2R)-2-acetyl-8-benzyloxy-2-(t-butyldimethylsilyloxy)-5-methoxy-1,2,3,4-tetrahydronaphthalene

(-)-(2R,1'S)-8-benzyloxy-2-(1'-hydroxyethyl)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

(2R,1'R)-(-)-8-(benzyloxy)-2-(1'-hydroxyethyl)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

(4R,5R)-(-)-8'-(benzyloxy)-5'-methoxy-2,2,5-trimethyl-3',4'-dihydrospiro<1,3-dioxolane-4,2'(1'H)-naphthalene>