Benzoic acid (1R,2S)-3-benzyloxy-1-[(S)-2-(dimethyl-hydrazono)-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-butyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2S)-3-benzyloxy-1-[(S)-2-(dimethyl-hydrazono)-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-butyl ester
• CAS No.: 671792-47-5
• Molecular Formula: C₃₅H₄₈N₂O₄S
• Molecular Weight: 592.843

Synonyms:

Chemical Property of Benzoic acid (1R,2S)-3-benzyloxy-1-[(S)-2-(dimethyl-hydrazono)-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,2S)-3-benzyloxy-1-[(S)-2-(dimethyl-hydrazono)-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-butyl ester

There total 8 articles about Benzoic acid (1R,2S)-3-benzyloxy-1-[(S)-2-(dimethyl-hydrazono)-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-butyl 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:

benzoyl chloride (98-88-4) + (2R,3S)-4-Benzyloxy-1-[(S)-2-(dimethyl-hydrazono)-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-yl]-4-methyl-3-methylsulfanylmethoxy-pentan-2-ol → Benzoic acid (1R,2S)-3-benzyloxy-1-[(S)-2-(dimethyl-hydrazono)-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-butyl ester (671792-47-5)

Guidance literature:

With 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1002/hlca.200390328

Reference yield:

(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol (139629-93-9) → Benzoic acid (1R,2S)-3-benzyloxy-1-[(S)-2-(dimethyl-hydrazono)-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-butyl ester (671792-47-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / O₃; PPh₃ / CH₂Cl₂ / 1.5 h / -78 °C

2: 90 percent / tetrahydrofuran; diethyl ether / 1 h / 20 °C

3: 58 percent / AcOH; Ac₂O / 38 h / 20 °C

4: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

5: 90 percent / (+)-camphorsulfonic acid / methanol; H₂O / 2.5 h / 65 °C

6: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr

7: LiNEt₂; DMPU / tetrahydrofuran; hexane / 17 h / -40 - 65 °C

8: DMPA / CH₂Cl₂ / 18 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; lithium diethylamide; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; acetic acid; (+)-10-camphorsulfonic acid; triphenylphosphine; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water;

DOI:10.1002/hlca.200390328

Reference yield:

(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-hydroxypropan-2-one (83657-30-1) → Benzoic acid (1R,2S)-3-benzyloxy-1-[(S)-2-(dimethyl-hydrazono)-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-butyl ester (671792-47-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / tetrahydrofuran; diethyl ether / 1 h / 20 °C

2: 58 percent / AcOH; Ac₂O / 38 h / 20 °C

3: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

4: 90 percent / (+)-camphorsulfonic acid / methanol; H₂O / 2.5 h / 65 °C

5: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr

6: LiNEt₂; DMPU / tetrahydrofuran; hexane / 17 h / -40 - 65 °C

7: DMPA / CH₂Cl₂ / 18 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; lithium diethylamide; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; (+)-10-camphorsulfonic acid; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water;

DOI:10.1002/hlca.200390328

upstream raw materials:

benzoyl chloride

(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol

(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-hydroxypropan-2-one

(+)-(2R)-2-{(1S)-2-(benzyloxy)-2-methyl-1-[(methylsulfanyl)methoxy]propyl}-oxirane

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