(1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-8-ene

Base Information

• Chemical Name: (1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-8-ene
• CAS No.: 176659-50-0
• Molecular Formula: C₂₈H₃₄O₄
• Molecular Weight: 434.576

Synonyms:(1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-8-ene

Chemical Property of (1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-8-ene

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Technology Process of (1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-8-ene

There total 3 articles about (1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-8-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: 99.0%

benzyl bromide (100-39-0) + ((1S,2S,6R,7R,8R,9S)-9-Hydroxymethyl-4,4,7-trimethyl-3,5-dioxa-tricyclo[5.2.2.02,6]undec-10-en-8-yl)-methanol (176659-49-7) → (1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.02,6]undec-8-ene (176659-50-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 18 ℃; for 18h;

DOI:10.1039/cc9960000869

Reference yield:

(3aR,7aS)-2,2,4-trimethyl-3a,7a-dihydro-1,3-benzodioxole (114763-30-3) → (1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.02,6]undec-8-ene (176659-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / CH₂Cl₂ / 24 h / 0 - 18 °C

2: 88 percent / LiAlH₄ / tetrahydrofuran / 3 h / 66 °C

3: 99 percent / NaH, Bu₄NI / dimethylformamide / 18 h / 0 - 18 °C

With lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/cc9960000869

Reference yield:

C14H16O5 (176659-48-6) → (1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.02,6]undec-8-ene (176659-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / LiAlH₄ / tetrahydrofuran / 3 h / 66 °C

2: 99 percent / NaH, Bu₄NI / dimethylformamide / 18 h / 0 - 18 °C

With lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/cc9960000869

upstream raw materials:

benzyl bromide

((1S,2S,6R,7R,8R,9S)-9-Hydroxymethyl-4,4,7-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-methanol

(3aR,7aS)-2,2,4-trimethyl-3a,7a-dihydro-1,3-benzodioxole

C₁₄H₁₆O₅

Downstream raw materials:

(1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-diol

(1R,4S,7R,8R)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-en-2-one

(1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one

(1R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-3-hydroxy-1-methyl-bicyclo[2.2.2]oct-5-en-2-one

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