(2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol

Base Information

Chemical Name:(2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol
CAS No.:444809-25-0
Molecular Formula:C₂₁H₂₈O₅
Molecular Weight:360.45
Hs Code.:

Synonyms:(2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol

Suppliers and Price of (2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol

There total 17 articles about (2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol 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: 60.0%

: 444809-24-9
(2S,3S,8aR)-2-Benzyloxymethyl-5-(3,4-dimethoxy-benzyloxymethyl)-3-hydroxy-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

: 444809-25-0
(2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 0.333333h;
DOI:10.1021/ol026159t

Reference yield:

: 6553-64-6
6,6-Dimethyl-2-cyclohexen-1-one

: 444809-25-0
(2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 78 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2.1: 90 percent / PCC / CH₂Cl₂ / 12 h / 20 °C

3.1: 60 percent / pyridinium tribromide; pyridine / CH₂Cl₂ / 20 h / 20 - 40 °C

4.1: 92 percent / (S)-CBS; BH₃*THF / tetrahydrofuran / 2 h / 20 °C

5.1: 85 percent / imidazole / dimethylformamide / 2 h / 20 - 40 °C

6.1: 70 percent / MgBr₂*Et₂O; BuSH / diethyl ether / 12 h / 20 °C

7.1: 95 percent / NaH / tetrahydrofuran / 8 h / 20 °C

8.1: t-BuLi / diethyl ether / 0.5 h / -78 °C

8.2: 60 percent / TMEDA / 0.5 h / -78 °C

9.1: 90 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

10.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

11.1: 77 percent / aq. HCl / propan-2-ol / 3 h / 0 - 20 °C

12.1: 60 percent / DDQ / CH₂Cl₂; H₂O / 0.33 h / 0 - 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; n-butyllithium; borane-THF; (S)-diphenylprolinol; n-butanethiol; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridinium hydrobromide perbromide; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/ol026159t

Reference yield:

: 62311-52-8
(2E) 1-benzyloxy-2-methyl-2-buten-4-ol

: 444809-25-0
(2S,3S,3aS,8aR)-2-Benzyloxymethyl-2,6,6-trimethyl-2,3,6,7,8,8a-hexahydro-5H-furo[2,3,4-de]chromene-3,3a-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 92 percent / TBHP; (-)-DIPT; Ti(O-i-Pr)4 / CH₂Cl₂ / 3 h / -18 °C

2.1: 75 percent / Pyr*SO₃; Et₃N; DMSO / CH₂Cl₂ / 1 h / 0 °C

3.1: t-BuLi / diethyl ether / 0.5 h / -78 °C

3.2: 60 percent / TMEDA / 0.5 h / -78 °C

4.1: 90 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

5.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

6.1: 77 percent / aq. HCl / propan-2-ol / 3 h / 0 - 20 °C

7.1: 60 percent / DDQ / CH₂Cl₂; H₂O / 0.33 h / 0 - 20 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; tetrabutyl ammonium fluoride; tert.-butyl lithium; sulfur trioxide pyridine complex; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; isopropyl alcohol;
DOI:10.1021/ol026159t