(2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

Base Information

Chemical Name:(2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate
CAS No.:1352492-34-2
Molecular Formula:C₃₅H₃₇NO₆Si
Molecular Weight:595.767
Hs Code.:

Synonyms:(2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

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Chemical Property of (2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

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Technology Process of (2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

There total 5 articles about (2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate 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: 80.0%

: 1352492-33-1
(2S,4R,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-ol

: 62-23-7
4-nitro-benzoic acid

: 1352492-34-2
(2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In toluene; at 20 ℃; for 0.25h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.10.006

Reference yield:

: 1352492-31-9
(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one

: 1352492-34-2
(2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 4 steps

1: silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Darkness; Inert atmosphere

2: palladium 10% on activated carbon; hydrogen; triethylamine / ethanol / 6 h / 20 °C / Inert atmosphere

3: sodium tetrahydroborate; cerium(III) chloride / methanol / -78 °C / Inert atmosphere

4: triphenylphosphine; diethylazodicarboxylate / toluene / 0.25 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; cerium(III) chloride; palladium 10% on activated carbon; hydrogen; silver trifluoromethanesulfonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In methanol; ethanol; dichloromethane; toluene; 4: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2011.10.006

Reference yield:

: 536-74-3
phenylacetylene

: 1352492-34-2
(2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C / Inert atmosphere

1.2: 8 h / -78 - 20 °C / Inert atmosphere

2.1: silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Darkness; Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethanol / 6 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate; cerium(III) chloride / methanol / -78 °C / Inert atmosphere

5.1: triphenylphosphine; diethylazodicarboxylate / toluene / 0.25 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; palladium 10% on activated carbon; hydrogen; silver trifluoromethanesulfonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; 5.1: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2011.10.006