Acetic acid (2S,3S,3aS,3bR,6aS,7aS)-4-[2-[3,3-dimethyl-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-2-hydroxy-5-oxo-octahydro-difuro[2,3-b;3',2'-d]furan-3-yl ester

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Chemical Name:Acetic acid (2S,3S,3aS,3bR,6aS,7aS)-4-[2-[3,3-dimethyl-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-2-hydroxy-5-oxo-octahydro-difuro[2,3-b;3',2'-d]furan-3-yl ester
CAS No.:170238-34-3
Molecular Formula:C₂₀H₂₆O₇
Molecular Weight:378.422
Hs Code.:

Synonyms:Acetic acid (2S,3S,3aS,3bR,6aS,7aS)-4-[2-[3,3-dimethyl-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-2-hydroxy-5-oxo-octahydro-difuro[2,3-b;3',2'-d]furan-3-yl ester

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Chemical Property of Acetic acid (2S,3S,3aS,3bR,6aS,7aS)-4-[2-[3,3-dimethyl-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-2-hydroxy-5-oxo-octahydro-difuro[2,3-b;3',2'-d]furan-3-yl ester

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Technology Process of Acetic acid (2S,3S,3aS,3bR,6aS,7aS)-4-[2-[3,3-dimethyl-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-2-hydroxy-5-oxo-octahydro-difuro[2,3-b;3',2'-d]furan-3-yl ester

There total 13 articles about Acetic acid (2S,3S,3aS,3bR,6aS,7aS)-4-[2-[3,3-dimethyl-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-2-hydroxy-5-oxo-octahydro-difuro[2,3-b;3',2'-d]furan-3-yl 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:

: 26532-25-2,36872-03-4
(E)-3,3-Dimethylcyclohexane-Δ^1,?-acetaldehyde

: 170238-34-3
Acetic acid (2S,3S,3aS,3bR,6aS,7aS)-4-[2-[3,3-dimethyl-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-2-hydroxy-5-oxo-octahydro-difuro[2,3-b;3',2'-d]furan-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-BuLi, 2.) ZnCl₂

2: 91 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / 0.67 h / 23 °C

3: 91 percent / diazobicycloundecane / dimethylformamide; 1,2-dimethoxy-ethane / 3 h / 80 °C

4: dimethyldioxirane / CH₂Cl₂ / 0.33 h / -20 °C

5: CH₂Cl₂ / 1.) -30 deg C, 1 h, 2.) -15 deg C, 3.5 h

With dmap; n-butyllithium; diazobicycloundecane; 3,3-dimethyldioxirane; triethylamine; zinc(II) chloride; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00142a051

Reference yield:

: 170238-24-1
(3aS,3bR,6aS,7aS)-3a,3b,6a,7a-Tetrahydro-3H-difuro[2,3-b;3',2'-d]furan-2-one

: 170238-34-3
Acetic acid (2S,3S,3aS,3bR,6aS,7aS)-4-[2-[3,3-dimethyl-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-2-hydroxy-5-oxo-octahydro-difuro[2,3-b;3',2'-d]furan-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-BuLi, 2.) ZnCl₂

2: 91 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / 0.67 h / 23 °C

3: 91 percent / diazobicycloundecane / dimethylformamide; 1,2-dimethoxy-ethane / 3 h / 80 °C

4: dimethyldioxirane / CH₂Cl₂ / 0.33 h / -20 °C

5: CH₂Cl₂ / 1.) -30 deg C, 1 h, 2.) -15 deg C, 3.5 h

With dmap; n-butyllithium; diazobicycloundecane; 3,3-dimethyldioxirane; triethylamine; zinc(II) chloride; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00142a051

Reference yield:

: 170238-18-3
((1R,3S,3aS,7aR)-1,3-Dimethoxy-1,3,3a,4,7,7a-hexahydro-isobenzofuran-5-ylmethyl)-trimethyl-silane

: 170238-34-3
Acetic acid (2S,3S,3aS,3bR,6aS,7aS)-4-[2-[3,3-dimethyl-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-2-hydroxy-5-oxo-octahydro-difuro[2,3-b;3',2'-d]furan-3-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) dimethyldioxirane, 2.) n-Bu₄NF / 1.) acetone, 0 deg C, 15 min, 2.) THF, 0 deg C, 40 min

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

3: 68 percent / MeSO₃H, 4A molecular sieves / CH₂Cl₂ / 1 h / -20 °C

4: 52 percent / BF₃*Et₂O / CH₂Cl₂ / 1.75 h / 0 °C

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

6: CHCl₃ / 14 h / 65 °C

7: 1.) n-BuLi, 2.) ZnCl₂

8: 91 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / 0.67 h / 23 °C

9: 91 percent / diazobicycloundecane / dimethylformamide; 1,2-dimethoxy-ethane / 3 h / 80 °C

10: dimethyldioxirane / CH₂Cl₂ / 0.33 h / -20 °C

11: CH₂Cl₂ / 1.) -30 deg C, 1 h, 2.) -15 deg C, 3.5 h

With dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; methanesulfonic acid; 4 A molecular sieve; diazobicycloundecane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; 3,3-dimethyldioxirane; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; In 1,2-dimethoxyethane; dichloromethane; chloroform; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja00142a051