(3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

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Chemical Name:(3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one
CAS No.:412342-79-1
Molecular Formula:C₂₀H₂₇IO₄
Molecular Weight:458.336
Hs Code.:

Synonyms:(3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

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Chemical Property of (3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

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Technology Process of (3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

There total 7 articles about (3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one 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:

: (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-hex-5-en-3-ol

: 412342-79-1
(3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 92 percent / TfOH / CH₂Cl₂ / 3.5 h / 20 °C

2.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 0 - 20 °C

2.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

3.1: PDC / dimethylformamide / 48 h / 20 °C

4.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

5.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

5.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

6.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

7.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

With dipyridinium dichromate; trifluorormethanesulfonic acid; Li(Pr-i)2; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol017266a

Reference yield:

: 412342-77-9
((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane

: 412342-79-1
(3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 0 - 20 °C

1.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

2.1: PDC / dimethylformamide / 48 h / 20 °C

3.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

4.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

4.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

5.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

6.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

With dipyridinium dichromate; Li(Pr-i)2; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol017266a

Reference yield:

: (3S,4S,5R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexan-1-ol

: 412342-79-1
(3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: PDC / dimethylformamide / 48 h / 20 °C

2.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

3.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

3.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

4.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

5.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

With dipyridinium dichromate; Li(Pr-i)2; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; 20percent Pd(OH)2/C; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol017266a