(3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene

Base Information

Chemical Name:(3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene
CAS No.:352422-90-3
Molecular Formula:C₂₅H₂₆O₇
Molecular Weight:438.477
Hs Code.:

Synonyms:(3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene

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Chemical Property of (3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene

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Technology Process of (3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene

There total 14 articles about (3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene 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:

: 100-39-0
benzyl bromide

: 352422-90-3
(3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

1.2: 27 / 16 h / 20 °C

2.1: water; acetic acid / 16 h / 90 °C

3.1: pyridine / 16 h / 20 °C

With pyridine; sodium hydride; In water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1039/b101364p

Reference yield:

: 96212-44-1
(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

: 352422-90-3
(3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: periodic acid / ethyl acetate / 1 h / 20 °C

2.1: tetrahydrofuran / 48 h / 20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride / dichloromethane / 1 h / 40 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

4.2: 27 / 16 h / 20 °C

5.1: water; acetic acid / 16 h / 90 °C

6.1: pyridine / 16 h / 20 °C

With pyridine; sodium hydride; periodic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; In tetrahydrofuran; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; 2.1: Grignard addition;
DOI:10.1039/b101364p

Reference yield:

: 51996-47-5
(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]-dioxol-6-ol

: 352422-90-3
(3R/S,1R,4R,5R,8R)-3,4-Diacetoxy-5,8-bis(benzyloxy)-2-oxabicyclo[3.3.0]oct-6-ene

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

1.2: 27 / 16 h / 20 °C

2.1: periodic acid / ethyl acetate / 1 h / 20 °C

3.1: tetrahydrofuran / 48 h / 20 °C

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride / dichloromethane / 1 h / 40 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

5.2: 27 / 16 h / 20 °C

6.1: water; acetic acid / 16 h / 90 °C

7.1: pyridine / 16 h / 20 °C

With pyridine; sodium hydride; periodic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; In tetrahydrofuran; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; 3.1: Grignard addition;
DOI:10.1039/b101364p