benzyl 2-((2R,6S)-6-((R)-2-(benzyloxy)pent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

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Chemical Name:benzyl 2-((2R,6S)-6-((R)-2-(benzyloxy)pent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate
CAS No.:864498-88-4
Molecular Formula:C₂₈H₃₆O₄
Molecular Weight:436.591
Hs Code.:

Synonyms:benzyl 2-((2R,6S)-6-((R)-2-(benzyloxy)pent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

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Chemical Property of benzyl 2-((2R,6S)-6-((R)-2-(benzyloxy)pent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

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Technology Process of benzyl 2-((2R,6S)-6-((R)-2-(benzyloxy)pent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

There total 13 articles about benzyl 2-((2R,6S)-6-((R)-2-(benzyloxy)pent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate 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: 90.0%

: benzyl 2-((2R,6S)-6-((R)-2-hydroxypent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

: 100-39-0
benzyl bromide

: 864498-88-4
benzyl 2-((2R,6S)-6-((R)-2-(benzyloxy)pent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

Guidance literature:: benzyl 2-((2R,6S)-6-((R)-2-hydroxypent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.333333h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol201863b

Reference yield:

: 1325653-68-6
C₁₃H₂₀O₂Si

: 864498-88-4
benzyl 2-((2R,6S)-6-((R)-2-(benzyloxy)pent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyridine; dmap / dichloromethane / 72 h / 20 °C / Inert atmosphere

2.1: pyridine / tetrahydrofuran / 12 h / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; benzene / 3 h / -78 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene; water / tert-butyl alcohol / 0 - 20 °C / Inert atmosphere

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0 - 20 °C / Inert atmosphere

8.1: N,N-dimethyl-formamide / 48 h / 70 °C / Inert atmosphere

9.1: pyridine; sodium hypophosphite monohydrate / water; acetic acid / 6 h / 50 °C / Inert atmosphere

10.1: diethyl ether / 3 h / -78 °C / Inert atmosphere

11.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

11.2: 2 h / 0 °C / Inert atmosphere

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; sodium hypophosphite monohydrate; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; water; hydrogen; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 5.1: Swern oxidation / 5.2: Swern oxidation / 6.1: Pinnick oxidation;
DOI:10.1021/ol201863b

Reference yield:

: 1350890-03-7
C₂₂H₃₀O₄SSi

: 864498-88-4
benzyl 2-((2R,6S)-6-((R)-2-(benzyloxy)pent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: pyridine / tetrahydrofuran / 12 h / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; benzene / 3 h / -78 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene; water / tert-butyl alcohol / 0 - 20 °C / Inert atmosphere

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0 - 20 °C / Inert atmosphere

7.1: N,N-dimethyl-formamide / 48 h / 70 °C / Inert atmosphere

8.1: pyridine; sodium hypophosphite monohydrate / water; acetic acid / 6 h / 50 °C / Inert atmosphere

9.1: diethyl ether / 3 h / -78 °C / Inert atmosphere

10.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

10.2: 2 h / 0 °C / Inert atmosphere

With pyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; sodium hypophosphite monohydrate; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; water; hydrogen; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 4.1: Swern oxidation / 4.2: Swern oxidation / 5.1: Pinnick oxidation;
DOI:10.1021/ol201863b