((2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-methanol

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Chemical Name:((2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-methanol
CAS No.:259231-50-0
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

Synonyms:((2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-methanol

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Chemical Property of ((2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-methanol

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Technology Process of ((2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-methanol

There total 10 articles about ((2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-methanol 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%

: 259231-49-7
(2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-2-trityloxymethyl-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocycloheptene

: 259231-50-0
((2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-methanol

Guidance literature:: With toluene-4-sulfonic acid; In methanol; dichloromethane;
DOI:10.1055/s-1999-3174

Reference yield:

: 100-39-0
benzyl bromide

: 259231-50-0
((2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-methanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: Bu₂SnO / methanol / Heating

1.2: 73 percent / CsF / dimethylformamide

2.1: 90 percent / imidazole / dimethylformamide / 50 °C

3.1: 100 percent / 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / 0 °C

4.1: 77 percent / tetrahydrofuran / 0.17 h

5.1: 97 percent / NaH / dimethylformamide

6.1: 99 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 2 h

7.1: 84 percent / TBAF / tetrahydrofuran

8.1: 88 percent / NaH / dimethylformamide

9.1: 94 percent / TsOH / methanol; CH₂Cl₂

With 1H-imidazole; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Metallation / 1.2: Etherification / 2.1: Etherification / 3.1: Epoxidation / 4.1: Substitution / 5.1: Etherification / 6.1: Ring-closing metathesis / 7.1: Desilylation / 8.1: Etherification / 9.1: Detritylation;
DOI:10.1055/s-1999-3174

Reference yield:

: 122350-80-5
1,5-anhydro-2-deoxy-6-O-trityl-D-arabino-hex-1-enitol

: 259231-50-0
((2R,3R,4R,4aS,9aS)-3-Allyloxy-4-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-methanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: Bu₂SnO / methanol / Heating

1.2: 73 percent / CsF / dimethylformamide

2.1: 90 percent / imidazole / dimethylformamide / 50 °C

3.1: 100 percent / 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / 0 °C

4.1: 77 percent / tetrahydrofuran / 0.17 h

5.1: 97 percent / NaH / dimethylformamide

6.1: 99 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 2 h

7.1: 84 percent / TBAF / tetrahydrofuran

8.1: 88 percent / NaH / dimethylformamide

9.1: 94 percent / TsOH / methanol; CH₂Cl₂

With 1H-imidazole; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Metallation / 1.2: Etherification / 2.1: Etherification / 3.1: Epoxidation / 4.1: Substitution / 5.1: Etherification / 6.1: Ring-closing metathesis / 7.1: Desilylation / 8.1: Etherification / 9.1: Detritylation;
DOI:10.1055/s-1999-3174