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

Base Information

Chemical Name:(2R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-3,6-dihydro-2H-2-pyranyl acetate
CAS No.:852925-25-8
Molecular Formula:C₂₀H₂₆O₆
Molecular Weight:362.423
Hs Code.:

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

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

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

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

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

Guidance literature:: Multi-step reaction with 3 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

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; nickel diacetate; diisobutylaluminium hydride; ethylenediamine; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1021/ol050477l

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 4 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

With sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; nickel diacetate; diisobutylaluminium hydride; ethylenediamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;
DOI:10.1021/ol050477l

Reference yield:

: 852925-23-6
(1R,2Z)-1-(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl-2-pentene-1,5-diol

: 108-24-7
acetic anhydride

: 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

Guidance literature:: (1R,2Z)-1-(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl-2-pentene-1,5-diol; With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h;

acetic anhydride; With pyridine; dmap; In dichloromethane; toluene; at -78 - 20 ℃; for 14h;
DOI:10.1021/ol050477l