(2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate

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Chemical Name:(2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate
CAS No.:864719-71-1
Molecular Formula:C₂₁H₂₈O₇
Molecular Weight:392.449
Hs Code.:

Synonyms:(2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate

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Chemical Property of (2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate

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Technology Process of (2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate

There total 9 articles about (2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate 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: 96.0%

: 864719-70-0
(2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-2-yl)acetate

: 864719-71-1
(2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 0 ℃;
DOI:10.1016/j.tet.2005.06.034

Reference yield:

: 864719-62-0
tert-butyl(dimethyl)silyl (2R,3R)-2-vinyltetrahydro-2H-pyran-3-yl ether

: 864719-71-1
(2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C

1.2: aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0 - 20 °C

2.1: 1.28 g / NaIO₄; RuCl₃*xH₂O / acetonitrile; CCl₄; H₂O

3.1: 96 percent / DMAP; camphorsulfonic acid; DCC / CH₂Cl₂ / 5 h / 20 °C

4.1: 96 percent / HF / acetonitrile / 0 °C

With dmap; ruthenium trichloride; sodium periodate; camphor-10-sulfonic acid; hydrogen fluoride; 9-bora-bicyclo[3.3.1]nonane; dicyclohexyl-carbodiimide; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2005.06.034

Reference yield:

: 918958-20-0
3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran

: 864719-71-1
(2R,3R)-2-[2-(benzyloxy)-2-oxoethyl]tetrahydro-2H-pyran-3-yl ((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 85 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 0.08 h / 0 °C

2.1: oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h

3.2: 1.28 g / tetrahydrofuran; hexane / 2 h

4.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C

4.2: aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0 - 20 °C

5.1: 1.28 g / NaIO₄; RuCl₃*xH₂O / acetonitrile; CCl₄; H₂O

6.1: 96 percent / DMAP; camphorsulfonic acid; DCC / CH₂Cl₂ / 5 h / 20 °C

7.1: 96 percent / HF / acetonitrile / 0 °C

With dmap; ruthenium trichloride; sodium periodate; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen fluoride; dimethyl sulfoxide; 9-bora-bicyclo[3.3.1]nonane; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; water; acetonitrile; 2.1: Swern oxidation / 3.2: Wittig methylenation;
DOI:10.1016/j.tet.2005.06.034