[(1S,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]oct-1-yl]-methanol

Base Information

Chemical Name:[(1S,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]oct-1-yl]-methanol
CAS No.:1026868-84-7
Molecular Formula:C₂₃H₃₄O₅S
Molecular Weight:422.586
Hs Code.:

Synonyms:[(1S,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]oct-1-yl]-methanol

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Chemical Property of [(1S,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]oct-1-yl]-methanol

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Technology Process of [(1S,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]oct-1-yl]-methanol

There total 15 articles about [(1S,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]oct-1-yl]-methanol 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:

: 160714-26-1
(1R,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]octane-1-carboxylic acid methyl ester

: 1026868-84-7
[(1S,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]oct-1-yl]-methanol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
DOI:10.1021/jo00098a009

Reference yield:

: 160714-20-5
(3R,3aR,7aR)-3-Methyl-7a-prop-2-ynyl-3a,7a-dihydro-3H,4H-isobenzofuran-1,7-dione

: 1026868-84-7
[(1S,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]oct-1-yl]-methanol

Guidance literature:: Multi-step reaction with 10 steps

1: 63 percent / NaBH₄, CeCl₃*7H₂O / methanol

2: 87 percent / NaAuCl₄*H₂O, H₂O / tetrahydrofuran / 60 °C

3: 86 percent / SmI₂, HMPA / tetrahydrofuran

4: (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

5: 1 N KOH / methanol / 80 °C

6: diethyl ether / Ambient temperature

7: Jones reagent / acetone / 0 °C

8: LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

9: tetrahydrofuran / -20 °C

10: DIBAL / CH₂Cl₂ / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; jones reagent; samarium diiodide; cerium(III) chloride; sodium tetrachloroaurate dihydrate; water; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;
DOI:10.1021/jo00098a009

Reference yield:

: 160714-21-6
(3R,3aR,7R,7aR)-7-Hydroxy-3-methyl-7a-prop-2-ynyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one

: 1026868-84-7
[(1S,2R,5R,6R,8R)-6,8-Bis-methoxymethoxy-6-methyl-2-(1-phenylsulfanylmethyl-vinyl)-bicyclo[3.2.1]oct-1-yl]-methanol

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / NaAuCl₄*H₂O, H₂O / tetrahydrofuran / 60 °C

2: 86 percent / SmI₂, HMPA / tetrahydrofuran

3: (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

4: 1 N KOH / methanol / 80 °C

5: diethyl ether / Ambient temperature

6: Jones reagent / acetone / 0 °C

7: LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

8: tetrahydrofuran / -20 °C

9: DIBAL / CH₂Cl₂ / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; jones reagent; samarium diiodide; sodium tetrachloroaurate dihydrate; water; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;
DOI:10.1021/jo00098a009