(2R,3R,4R,6R)-3-hydroxy-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

Base Information

Chemical Name:(2R,3R,4R,6R)-3-hydroxy-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate
CAS No.:1067881-67-7
Molecular Formula:C₂₁H₂₃NO₈
Molecular Weight:417.416
Hs Code.:

Synonyms:(2R,3R,4R,6R)-3-hydroxy-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

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Chemical Property of (2R,3R,4R,6R)-3-hydroxy-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

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Technology Process of (2R,3R,4R,6R)-3-hydroxy-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

There total 3 articles about (2R,3R,4R,6R)-3-hydroxy-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-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: 70.0%

: 1067881-66-6
(2R,3S,4S,6R)-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diol

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

: 1067881-67-7
(2R,3R,4R,6R)-3-hydroxy-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol801817f

Reference yield:

: 1067881-64-4
(2R,6R)-6-(4-methoxybenzyloxy)-3,6-dihydro-2-methyl-2H-pyran-3-ol

: 1067881-67-7
(2R,3R,4R,6R)-3-hydroxy-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 3 steps

1: triphenylphosphine; 4-methyl-morpholine; di-isopropyl azodicarboxylate; 2-nitrobenzenesulfonyl hydrazide / 2.17 h / -30 °C / Inert atmosphere

2: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol; acetone; water / 12 h / 0 °C

3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 24 h / 0 - 20 °C

With 4-methyl-morpholine; osmium(VIII) oxide; di-isopropyl azodicarboxylate; 2-nitrobenzenesulfonyl hydrazide; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; water; acetone; tert-butyl alcohol; 2: |Upjohn Dihydroxylation / 3: |Mitsunobu Displacement;
DOI:10.1039/c3cc44050h

Reference yield:

: 1067881-65-5
(2R,6R)-2-((4-methoxybenzyl)oxy)-6-methyl-3,6-dihydro-2H-pyran

: 1067881-67-7
(2R,3R,4R,6R)-3-hydroxy-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol; acetone; water / 12 h / 0 °C

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 24 h / 0 - 20 °C

With osmium(VIII) oxide; di-isopropyl azodicarboxylate; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; water; acetone; tert-butyl alcohol; 1: |Upjohn Dihydroxylation / 2: |Mitsunobu Displacement;
DOI:10.1039/c3cc44050h