(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol

Base Information

Chemical Name:(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol
CAS No.:781652-08-2
Molecular Formula:C₂₁H₃₂O₃
Molecular Weight:332.483
Hs Code.:

Synonyms:(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol

Chemical Property:

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MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol

There total 9 articles about (R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-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: 70.0%

: ((E)-(R)-1-Benzyloxymethyl-but-2-enyl)-dimethyl-phenyl-silane

: 781651-86-3
Acetic acid (3S,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl ester

: 781652-08-2
(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol

: 781651-85-2
{(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propoxy}-triisopropyl-silane

Guidance literature:: With titanium(IV) trichloride isopropoxide; In dichloromethane; at -78 ℃;
DOI:10.1002/anie.200460434

Reference yield:

: (Z)-(S)-4-Methyl-5-triisopropylsilanyloxy-pent-2-en-1-ol

: 781652-08-2
(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: MCPBA / CH₂Cl₂ / -78 - -45 °C

2.1: tBuOK / tetrahydrofuran / -78 °C

3.1: dimethylformamide / 0 °C

4.1: H₂ / PtO₂ / ethanol / 20 °C

4.2: 89 percent / Ti(OiPr)4 / dimethylformamide / 100 °C

5.1: DIBAL-H / CH₂Cl₂ / -78 °C

6.1: pyridine; DMAP / -78 - 20 °C

7.1: 11 percent / TiCl₃(OiPr) / CH₂Cl₂ / -78 °C

With pyridine; dmap; titanium(IV) trichloride isopropoxide; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Swern oxidation / 3.1: Horner-Emmons reaction;
DOI:10.1002/anie.200460434

Reference yield:

: (2R,3R)-3-((R)-1-Methyl-2-triisopropylsilanyloxy-ethyl)-oxirane-2-carbaldehyde

: 781652-08-2
(R)-2-[(2S,5S,6S)-6-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-5-methyl-tetrahydro-pyran-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: tBuOK / tetrahydrofuran / -78 °C

2.1: dimethylformamide / 0 °C

3.1: H₂ / PtO₂ / ethanol / 20 °C

3.2: 89 percent / Ti(OiPr)4 / dimethylformamide / 100 °C

4.1: DIBAL-H / CH₂Cl₂ / -78 °C

5.1: pyridine; DMAP / -78 - 20 °C

6.1: 11 percent / TiCl₃(OiPr) / CH₂Cl₂ / -78 °C

With pyridine; dmap; titanium(IV) trichloride isopropoxide; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Horner-Emmons reaction;
DOI:10.1002/anie.200460434