(2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol
CAS No.:256327-46-5
Molecular Formula:C₂₉H₃₄O₇
Molecular Weight:494.585
Hs Code.:

Synonyms:(2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol

There total 6 articles about (2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-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: 95.0%

: 256327-59-0
[(2R,3R,4R,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

: 256327-46-5
(2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 1h;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H

Reference yield:

: 100-39-0
benzyl bromide

: 256327-46-5
(2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-Bu₂SnO / toluene / 3 h / 110 °C

1.2: 83 percent / n-Bu₄NI / toluene / 5 h / 25 - 110 °C

2.1: 93 percent / imidazole / 3 h / 0 - 25 °C

3.1: 97 percent / NMO; OsO₄; H₂O / acetone / 8 h / 25 °C

4.1: 95 percent / n-Bu₄NI; NaH / dimethylformamide / 3 h / 0 - 25 °C

5.1: 95 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 25 °C

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Oxidation / 4.1: Etherification / 5.1: Desilylation;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H

Reference yield:

: 120316-45-2
((2R,3R,4R)-4-Benzyloxy-2-methyl-3,4-dihydro-2H-pyran-3-yloxy)-tert-butyl-dimethyl-silane

: 256327-46-5
(2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / NMO; OsO₄; H₂O / acetone / 8 h / 25 °C

2: 95 percent / n-Bu₄NI; NaH / dimethylformamide / 3 h / 0 - 25 °C

3: 95 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 25 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; 1: Oxidation / 2: Etherification / 3: Desilylation;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H