(2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol

Base Information

• Chemical Name: (2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol
• CAS No.: 412342-80-4
• Molecular Formula: C₂₀H₃₁IO₄
• Molecular Weight: 462.368
• Mol file: 412342-80-4.mol

Synonyms:(2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol

Chemical Property of (2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol

There total 8 articles about (2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol 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 → (2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol (412342-80-4)

Guidance literature:

Multi-step reaction with 8 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

8.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

With dipyridinium dichromate; lithium borohydride; 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:

((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane (412342-77-9) → (2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol (412342-80-4)

Guidance literature:

Multi-step reaction with 7 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

7.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

With dipyridinium dichromate; lithium borohydride; 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 → (2S,3S,4S,5R)-2-((Z)-3-Iodo-2-methyl-allyl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexane-1,4-diol (412342-80-4)

Guidance literature:

Multi-step reaction with 6 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

6.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

With dipyridinium dichromate; lithium borohydride; 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

upstream raw materials:

(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

(4S,5S)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

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

(3S,4S,5R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexanoic acid

Downstream raw materials:

(4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

(2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-enoic acid ethyl ester

(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol