Acetic acid (R)-2-[3,3-dimethyl-cyclohex-(E)-ylidene]-1-((3S,3aR,3bR,6aS,7aS)-2-oxo-2,3,3a,3b,6a,7a-hexahydro-difuro[2,3-b;3',2'-d]furan-3-yl)-ethyl ester

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Chemical Name:Acetic acid (R)-2-[3,3-dimethyl-cyclohex-(E)-ylidene]-1-((3S,3aR,3bR,6aS,7aS)-2-oxo-2,3,3a,3b,6a,7a-hexahydro-difuro[2,3-b;3',2'-d]furan-3-yl)-ethyl ester
CAS No.:170238-33-2
Molecular Formula:C₂₀H₂₆O₆
Molecular Weight:362.423
Hs Code.:

Synonyms:Acetic acid (R)-2-[3,3-dimethyl-cyclohex-(E)-ylidene]-1-((3S,3aR,3bR,6aS,7aS)-2-oxo-2,3,3a,3b,6a,7a-hexahydro-difuro[2,3-b;3',2'-d]furan-3-yl)-ethyl ester

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Chemical Property of Acetic acid (R)-2-[3,3-dimethyl-cyclohex-(E)-ylidene]-1-((3S,3aR,3bR,6aS,7aS)-2-oxo-2,3,3a,3b,6a,7a-hexahydro-difuro[2,3-b;3',2'-d]furan-3-yl)-ethyl ester

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Technology Process of Acetic acid (R)-2-[3,3-dimethyl-cyclohex-(E)-ylidene]-1-((3S,3aR,3bR,6aS,7aS)-2-oxo-2,3,3a,3b,6a,7a-hexahydro-difuro[2,3-b;3',2'-d]furan-3-yl)-ethyl ester

There total 9 articles about Acetic acid (R)-2-[3,3-dimethyl-cyclohex-(E)-ylidene]-1-((3S,3aR,3bR,6aS,7aS)-2-oxo-2,3,3a,3b,6a,7a-hexahydro-difuro[2,3-b;3',2'-d]furan-3-yl)-ethyl 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: 91.0%

: 108-24-7
acetic anhydride

: 170238-25-2
(3S,3aR,3bR,6aS,7aS)-3-{(R)-2-[3,3-Dimethyl-cyclohex-(E)-ylidene]-1-hydroxy-ethyl}-3a,3b,6a,7a-tetrahydro-3H-difuro[2,3-b;3',2'-d]furan-2-one

: 170238-33-2
Acetic acid (R)-2-[3,3-dimethyl-cyclohex-(E)-ylidene]-1-((3S,3aR,3bR,6aS,7aS)-2-oxo-2,3,3a,3b,6a,7a-hexahydro-difuro[2,3-b;3',2'-d]furan-3-yl)-ethyl ester

Guidance literature:: With dmap; triethylamine; at 23 ℃; for 0.666667h;
DOI:10.1021/ja00142a051

Reference yield:

: (1S,3R,3aR,7aS)-1,3-Dimethoxy-6-methylene-octahydro-isobenzofuran-5-ol

: 170238-33-2
Acetic acid (R)-2-[3,3-dimethyl-cyclohex-(E)-ylidene]-1-((3S,3aR,3bR,6aS,7aS)-2-oxo-2,3,3a,3b,6a,7a-hexahydro-difuro[2,3-b;3',2'-d]furan-3-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / NaIO₄, OsO₄, H₂O / 2-methyl-propan-2-ol / 1 h / 23 °C

2: 68 percent / MeSO₃H, 4A molecular sieves / CH₂Cl₂ / 1 h / -20 °C

3: 52 percent / BF₃*Et₂O / CH₂Cl₂ / 1.75 h / 0 °C

4: m-chloroperbenzoic acid / CH₂Cl₂ / 1.5 h / -20 °C

5: CHCl₃ / 14 h / 65 °C

6: 1.) n-BuLi, 2.) ZnCl₂

7: 91 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / 0.67 h / 23 °C

With dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; methanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; water; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; In dichloromethane; chloroform; tert-butyl alcohol;
DOI:10.1021/ja00142a051

Reference yield:

: 170238-21-8
(3aS,3bR,5R,6aS,7aS)-5-Methoxy-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one

: 170238-33-2
Acetic acid (R)-2-[3,3-dimethyl-cyclohex-(E)-ylidene]-1-((3S,3aR,3bR,6aS,7aS)-2-oxo-2,3,3a,3b,6a,7a-hexahydro-difuro[2,3-b;3',2'-d]furan-3-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 52 percent / BF₃*Et₂O / CH₂Cl₂ / 1.75 h / 0 °C

2: m-chloroperbenzoic acid / CH₂Cl₂ / 1.5 h / -20 °C

3: CHCl₃ / 14 h / 65 °C

4: 1.) n-BuLi, 2.) ZnCl₂

5: 91 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / 0.67 h / 23 °C

With dmap; n-butyllithium; boron trifluoride diethyl etherate; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; In dichloromethane; chloroform;
DOI:10.1021/ja00142a051