(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

Base Information

Chemical Name:(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one
CAS No.:365212-89-1
Molecular Formula:C₂₃H₃₂O₅
Molecular Weight:388.504
Hs Code.:

Synonyms:(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

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Chemical Property of (2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

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Technology Process of (2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

There total 12 articles about (2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one 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: 97.0%

: 365212-82-4
(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

: 365212-89-1
(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1002/chem.200500993

Reference yield: 92.0%

: 365212-83-5
(2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one

: 365212-89-1
(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/ol016434w

Reference yield:

: C₂₄H₃₀O₅

: 365212-89-1
(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

Guidance literature:: Multi-step reaction with 8 steps

1: 6.5 g / diethyl ether / 0.5 h / -65 - 20 °C

2: 85 percent / (i-Pr)2NEt

3: TiCl₄; TMEDA; Zn / PbCl₂ / CH₂Cl₂

4: PhCH=RuCH{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 20 °C

5: 92 percent / m-CPBA

6: 78 percent / NaH / tetrahydrofuran

7: PPTS; pyridine / toluene / 100 °C

8: 97 percent / DDQ; H₂O / CH₂Cl₂

With pyridine; N,N,N,N,-tetramethylethylenediamine; water; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; benzene;
DOI:10.1002/chem.200500993