(+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate

Base Information

Chemical Name:(+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate
CAS No.:502613-93-6
Molecular Formula:C₃₆H₄₄O₇S
Molecular Weight:620.807
Hs Code.:

(+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate

Synonyms:(+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate

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Chemical Property of (+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate

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Technology Process of (+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate

There total 23 articles about (+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate 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: 91.0%

: Benzoic acid (1R,2S)-3-benzyloxy-1-((3aR,9aS,9bS)-1-hydroxy-9a,9b-dimethyl-7-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-butyl ester

: 502613-93-6
(+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate

Guidance literature:: With N-iodo-succinimide; tetra-(n-butyl)ammonium iodide; In dichloromethane; at 0 - 20 ℃; for 1h;
DOI:10.1002/hlca.200390328

Reference yield:

: 83657-30-1
(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-hydroxypropan-2-one

: 502613-93-6
(+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate

Guidance literature:: Multi-step reaction with 10 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; chiral octahydronaphthalene dimethylhydrazone / tetrahydrofuran; hexane / 17 h / -40 - 65 °C

7: DMAP / CH₂Cl₂ / 18 h / 20 °C

8: 615 mg / AcONa; AcOH / benzene / 45 h / 65 °C

9: 70 percent / aq. HClO₄ / acetonitrile / 1.25 h / 55 °C

10: 91 percent / N-iodosuccinimide; tetrabutylammonium iodide / CH₂Cl₂ / 1 h / 0 - 20 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-iodo-succinimide; perchloric acid; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; sodium acetate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; (+)-10-camphorsulfonic acid; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; benzene;
DOI:10.1002/hlca.200390328

Reference yield:

: 502614-16-6
(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-1-[(methylsulfanyl)methoxy]propan-2-ol

: 502613-93-6
(+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

2: 90 percent / (+)-camphorsulfonic acid / methanol; H₂O / 2.5 h / 65 °C

3: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr

4: LiNEt₂; DMPU; chiral octahydronaphthalene dimethylhydrazone / tetrahydrofuran; hexane / 17 h / -40 - 65 °C

5: DMAP / CH₂Cl₂ / 18 h / 20 °C

6: 615 mg / AcONa; AcOH / benzene / 45 h / 65 °C

7: 70 percent / aq. HClO₄ / acetonitrile / 1.25 h / 55 °C

8: 91 percent / N-iodosuccinimide; tetrabutylammonium iodide / CH₂Cl₂ / 1 h / 0 - 20 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-iodo-succinimide; perchloric acid; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; (+)-10-camphorsulfonic acid; N-tosylimidazole; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile; benzene;
DOI:10.1002/hlca.200390328