(Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate

Base Information

Chemical Name:(Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate
CAS No.:1375950-87-0
Molecular Formula:C₃₂H₄₈I₂O₄Si
Molecular Weight:778.625
Hs Code.:

(Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate

Synonyms:(Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate

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Chemical Property of (Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate

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Technology Process of (Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate

There total 14 articles about (Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate 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: 100.0%

: 1174549-23-5
(Z)-5-((tert-butyldimethylsilyl)oxy)-3-iodopent-2-enoic acid

: 1375951-00-0
(2R,4R,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-ol

: 1375950-87-0
(Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In benzene; at 20 ℃; for 1.5h;
DOI:10.1002/anie.201108749

Reference yield:

: 1375950-97-2
(2S,4R,6R)-2-(but-3-ynyl)-6-(3-(trimethylsilyl)prop-2-ynyl)tetrahydro-2H-pyran-4-ol

: 1375950-87-0
(Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -78 °C

2.1: zirconocene dichloride; tert-butyl alcohol / dichloromethane; toluene / 24 h / 0 - 20 °C / Inert atmosphere

2.2: 5 h / 0 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 60 h / 20 °C / Inert atmosphere

4.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

5.1: zirconocene dichloride; tert-butyl alcohol / dichloromethane; toluene / 0 - 20 °C / Inert atmosphere

5.2: -20 - 20 °C / Inert atmosphere

6.1: camphor-10-sulfonic acid / tetrahydrofuran; methanol / 2 h / 20 °C

7.1: di-isopropyl azodicarboxylate; triphenylphosphine / benzene / 1.5 h / 20 °C

With 2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; triphenylphosphine; tert-butyl alcohol; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; toluene; benzene; 3.1: Negishi coupling reaction / 7.1: Mitsunobu reaction;
DOI:10.1002/anie.201108749

Reference yield:

: 78592-82-2
4-(tert-butyldimethylsilyloxy)-1-butyne

: 1375950-87-0
(Z)-((2R,4S,6S)-2-((E)-3-iodo-2-methylallyl)-6-((E)-3-methyl-5-phenylpent-3-enyl)tetrahydro-2H-pyran-4-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -40 °C

1.2: 1.17 h / -45 - 20 °C

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether / 0.67 h / 0 - 20 °C / Inert atmosphere

2.2: 0.83 h / -50 °C / Inert atmosphere

3.1: manganese(IV) oxide / dichloromethane / 3 h / 0 - 20 °C

4.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 0.17 h / 0 °C

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / benzene / 1.5 h / 20 °C

With manganese(IV) oxide; sodium chlorite; n-butyllithium; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; di-isopropyl azodicarboxylate; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 4.1: Pinnick oxidation / 5.1: Mitsunobu reaction;
DOI:10.1002/anie.201108749