(5aS,7R,8S,11aR)-8-Benzyloxy-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-2-one

Base Information

Chemical Name:(5aS,7R,8S,11aR)-8-Benzyloxy-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-2-one
CAS No.:725253-47-4
Molecular Formula:C₂₆H₃₂O₅
Molecular Weight:424.537
Hs Code.:

Synonyms:(5aS,7R,8S,11aR)-8-Benzyloxy-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-2-one

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Chemical Property of (5aS,7R,8S,11aR)-8-Benzyloxy-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-2-one

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Technology Process of (5aS,7R,8S,11aR)-8-Benzyloxy-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-2-one

There total 4 articles about (5aS,7R,8S,11aR)-8-Benzyloxy-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-2-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: 94.0%

: 725253-46-3
4-((2S,3R,7S,8R)-7-Benzyloxy-8-benzyloxymethyl-3-hydroxy-oxocan-2-yl)-butyric acid

: 725253-47-4
(5aS,7R,8S,11aR)-8-Benzyloxy-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-2-one

Guidance literature:: 4-((2S,3R,7S,8R)-7-Benzyloxy-8-benzyloxymethyl-3-hydroxy-oxocan-2-yl)-butyric acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃;

With dmap; In toluene; at 110 ℃; Further stages.;
DOI:10.1016/j.tetlet.2004.04.083

Reference yield:

: 4-[(2S,3R,7S,8R)-7-Benzyloxy-8-benzyloxymethyl-3-(2-ethoxy-ethoxy)-oxocan-2-yl]-butyraldehyde

: 725253-47-4
(5aS,7R,8S,11aR)-8-Benzyloxy-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol / 0 - 20 °C

1.2: aq.HCl / H₂O; 2-methyl-propan-2-ol / 20 °C

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

2.2: 94 percent / DMAP / toluene / 110 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; water; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2004.04.083

Reference yield:

: [4-((Z)-(7S,8R)-7-Benzyloxy-8-benzyloxymethyl-5,6,7,8-tetrahydro-4H-oxocin-2-yl)-butoxy]-triisopropyl-silane

: 725253-47-4
(5aS,7R,8S,11aR)-8-Benzyloxy-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: thexylborane / tetrahydrofuran / 0 °C

1.2: 100 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 20 °C

2.1: PPTS / CH₂Cl₂ / 20 °C

3.1: TBAF / tetrahydrofuran / 20 °C

4.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0 °C

5.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol / 0 - 20 °C

5.2: aq.HCl / H₂O; 2-methyl-propan-2-ol / 20 °C

6.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

6.2: 94 percent / DMAP / toluene / 110 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridine-SO₃ complex; thexylborane; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2004.04.083