(1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane

Base Information

• Chemical Name: (1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane
• CAS No.: 154705-86-9
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.391

Synonyms:(1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane

Chemical Property of (1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane

Chemical Property:

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Technology Process of (1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane

There total 5 articles about (1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane 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: 93.0%

benzyl bromide (100-39-0) + (1R,2S,6S,7S,8R)-2-Furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecan-7-ol (154705-85-8) → (1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane (154705-86-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1039/c39930001839

Reference yield:

1,6-anhydro-3,4-O-isopropylidene-β-D-lyxo-hexopyranos-2-ulose (17073-94-8) → (1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane (154705-86-9)

Guidance literature:

Multi-step reaction with 3 steps

1: n-BuLi / tetrahydrofuran / -78 °C

2: 97 percent / p-TsOH / acetone

3: 93 percent / NaH / dimethylformamide

With n-butyllithium; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1039/c39930001839

Reference yield:

1,6-anhydro-β-D-galactopyranose (644-76-8) → (1R,2S,6S,7S,8R)-7-Benzyloxy-2-furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane (154705-86-9)

Guidance literature:

Multi-step reaction with 5 steps

1: p-TsOH

2: (COCl)2, DMSO / tetrahydrofuran / -60 - -20 °C

3: n-BuLi / tetrahydrofuran / -78 °C

4: 97 percent / p-TsOH / acetone

5: 93 percent / NaH / dimethylformamide

With n-butyllithium; oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1039/c39930001839

upstream raw materials:

benzyl bromide

(1R,2S,6S,7S,8R)-2-Furan-3-yl-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecan-7-ol

1,6-anhydro-3,4-O-isopropylidene-β-D-lyxo-hexopyranos-2-ulose

1,6-anhydro-β-D-galactopyranose

Downstream raw materials:

3-((1R,2S,6S,7S,8R)-7-Benzyloxy-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-2-yl)-5H-furan-2-one

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