(3R,4R)-3-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-hexadec-1-en-4-ol

Base Information

• Chemical Name: (3R,4R)-3-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-hexadec-1-en-4-ol
• CAS No.: 212205-72-6
• Molecular Formula: C₃₂H₄₉BrO₄
• Molecular Weight: 577.643

Synonyms:(3R,4R)-3-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-hexadec-1-en-4-ol

Chemical Property of (3R,4R)-3-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-hexadec-1-en-4-ol

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Technology Process of (3R,4R)-3-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-hexadec-1-en-4-ol

There total 2 articles about (3R,4R)-3-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-hexadec-1-en-4-ol 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: 82.0%

(2S,6R)-2-(4-Bromo-benzyloxymethyl)-6-[(R)-1-((1R,2R)-2-methoxymethoxy-1-vinyl-tetradecyloxy)-allyl]-3,6-dihydro-2H-pyran (212205-64-6) → (3R,4R)-3-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-hexadec-1-en-4-ol (212205-72-6)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at -30 ℃;

DOI:10.1021/jo9810765

Reference yield:

(S)-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-((1R,2R)-2-methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid methyl ester (212205-71-5) → (3R,4R)-3-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-hexadec-1-en-4-ol (212205-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DIBALH / 1.) toluene, -78 deg C, 2.) THF, -78 to 40 deg C

2: 82 percent / (CH₃)3SiBr / CH₂Cl₂ / -30 °C

With trimethylsilyl bromide; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/jo9810765

Reference yield: 99.0%

t-butyldimethylsiyl triflate (69739-34-0) + (3R,4R)-3-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-hexadec-1-en-4-ol (212205-72-6) → [(R)-1-((R)-1-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-allyl)-tridecyloxy]-tert-butyl-dimethyl-silane (212205-73-7)

Guidance literature:

With 2,6-dimethylpyridine; at 0 ℃;

DOI:10.1021/jo9810765

upstream raw materials:

(2S,6R)-2-(4-Bromo-benzyloxymethyl)-6-[(R)-1-((1R,2R)-2-methoxymethoxy-1-vinyl-tetradecyloxy)-allyl]-3,6-dihydro-2H-pyran

(S)-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-((1R,2R)-2-methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid methyl ester

Downstream raw materials:

[(R)-1-((R)-1-{(R)-1-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-allyloxy}-allyl)-tridecyloxy]-tert-butyl-dimethyl-silane

((R)-1-{(2R,5R)-5-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-2,5-dihydro-furan-2-yl}-tridecyloxy)-tert-butyl-dimethyl-silane

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