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

Base Information

Chemical Name:(2R,3S,4R,6R)-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diol
CAS No.:1447925-27-0
Molecular Formula:C₁₄H₂₀O₅
Molecular Weight:268.31
Hs Code.:

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

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Chemical Property of (2R,3S,4R,6R)-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diol

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Technology Process of (2R,3S,4R,6R)-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diol

There total 3 articles about (2R,3S,4R,6R)-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-3,4-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: 88.0%

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

: 1447925-27-0
(2R,3S,4R,6R)-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diol

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 1h;
DOI:10.1039/c3cc44050h

Reference yield:

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

: 1447925-27-0
(2R,3S,4R,6R)-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 4 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

4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C

With 4-methyl-morpholine; osmium(VIII) oxide; di-isopropyl azodicarboxylate; 2-nitrobenzenesulfonyl hydrazide; 4-methylmorpholine N-oxide; triphenylphosphine; lithium hydroxide; 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

: 1447925-27-0
(2R,3S,4R,6R)-6-((4-methoxybenzyl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 3 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

3: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C

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