(2R,4R,5R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate

Base Information

Chemical Name:(2R,4R,5R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate
CAS No.:852925-27-0
Molecular Formula:C₂₀H₂₈O₈
Molecular Weight:396.438
Hs Code.:

Synonyms:(2R,4R,5R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate

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Chemical Property of (2R,4R,5R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate

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Technology Process of (2R,4R,5R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate

There total 5 articles about (2R,4R,5R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl 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:

: 1-(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl-5-[(1,1,1-triisopropylsilyl)oxy]-2-pentyn-1-ol

: 852925-27-0
(2R,4R,5R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / NaBH₄; Ni(OAc)2*H₂O; H₂ / ethylenediamine / ethanol / 3 h / 20 °C / 760 Torr

2.1: 95 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

3.1: DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

3.2: pyridine; DMAP / CH₂Cl₂; toluene / 14 h / -78 - 20 °C

4.1: N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; acetone; H₂O / 16 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; hydrogen; nickel diacetate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; ethylenediamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/ol050477l

Reference yield:

: 81801-09-4
4-O-benzyl-2,3-O-isopropylidene-D-threose

: 852925-27-0
(2R,4R,5R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

1.2: Ti(i-PrO)4 / tetrahydrofuran; hexane; CH₂Cl₂ / 1.5 h / -78 °C

1.3: 66 percent / tetrahydrofuran; hexane; CH₂Cl₂ / -78 - 20 °C

2.1: 95 percent / NaBH₄; Ni(OAc)2*H₂O; H₂ / ethylenediamine / ethanol / 3 h / 20 °C / 760 Torr

3.1: 95 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

4.1: DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

4.2: pyridine; DMAP / CH₂Cl₂; toluene / 14 h / -78 - 20 °C

5.1: N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; acetone; H₂O / 16 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; nickel diacetate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; ethylenediamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/ol050477l

Reference yield:

: 852925-25-8
(2R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-3,6-dihydro-2H-2-pyranyl acetate

: 852925-27-0
(2R,4R,5R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate

: (2R,4S,5S,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 16h; Title compound not separated from byproducts;
DOI:10.1021/ol050477l