(1R,2R,6R,8R,9S)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

Base Information

• Chemical Name: (1R,2R,6R,8R,9S)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene
• CAS No.: 352422-87-8
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343

Synonyms:(1R,2R,6R,8R,9S)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

Chemical Property of (1R,2R,6R,8R,9S)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1R,2R,6R,8R,9S)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

There total 5 articles about (1R,2R,6R,8R,9S)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-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: 79.0%

(5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose (352422-85-6) → (1R,2R,6R,8R,9S)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02.6]undec-10-ene (352422-87-8)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 120h;

DOI:10.1039/b101364p

Reference yield:

(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 (96212-44-1) → (1R,2R,6R,8R,9S)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02.6]undec-10-ene (352422-87-8)

Guidance literature:

Multi-step reaction with 3 steps

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

2: tetrahydrofuran / 48 h / 20 °C

3: Grubbs catalyst first generation / dichloromethane / 120 h / 20 °C

With periodic acid; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; ethyl acetate; 2: Grignard addition;

DOI:10.1039/b101364p

Reference yield:

(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 (51996-47-5) → (1R,2R,6R,8R,9S)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02.6]undec-10-ene (352422-87-8)

Guidance literature:

Multi-step reaction with 4 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: Grubbs catalyst first generation / dichloromethane / 120 h / 20 °C

With sodium hydride; periodic acid; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3.1: Grignard addition;

DOI:10.1039/b101364p

upstream raw materials:

(5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose

(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

(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

benzyl bromide

Downstream raw materials:

(1R,2R,6R,8R,9R)-1-Benzyloxy-9-hydroxy-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

(1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

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

(1R,3R,5R,8R)-5,8-Bis(benzyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

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