Acetic acid (R)-2-[(4R,5R)-5-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

Base Information

Chemical Name:Acetic acid (R)-2-[(4R,5R)-5-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester
CAS No.:188343-71-7
Molecular Formula:C₁₉H₂₈O₆
Molecular Weight:352.428
Hs Code.:

Synonyms:Acetic acid (R)-2-[(4R,5R)-5-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

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Chemical Property of Acetic acid (R)-2-[(4R,5R)-5-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

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Technology Process of Acetic acid (R)-2-[(4R,5R)-5-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

There total 5 articles about Acetic acid (R)-2-[(4R,5R)-5-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester 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: 90.0%

: 75-36-5
acetyl chloride

: 188343-70-6
(R)-1-[(4R,5R)-5-(3-Benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethane-1,2-diol

: 188343-71-7
Acetic acid (R)-2-[(4R,5R)-5-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

Guidance literature:: With 2,4,6-trimethyl-pyridine; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1139/v97-010

Reference yield:

: 65371-70-2,77970-35-5,77970-36-6,88825-11-0
methyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-2-enonate

: 188343-71-7
Acetic acid (R)-2-[(4R,5R)-5-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / H₂ / Pd/C / ethanol / 18 h / 2068.6 Torr / Ambient temperature

2: 90 percent / LiAlH₄ / diethyl ether / a) 0 deg C, 0.5 h, 2.) RT, 14 h

3: 1.) NaH, 2.) Bu₄NI / 1.) THF, 0 deg C, 20 min, 2.) THF, a) 0 deg C, 30 min, b) RT, 24 h

4: 60 percent / Dowex 50W-X₈ resin / methanol; H₂O / 24 h

5: 90 percent / 2,4,6-collidine / CH₂Cl₂ / 2 h / -78 °C

With 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; Dowex 50W-X₈ resin; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; water;
DOI:10.1139/v97-010

Reference yield:

: 13039-93-5
2,2:4,5-di-O-isopropylidene-D-arabinose

: 188343-71-7
Acetic acid (R)-2-[(4R,5R)-5-(3-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / benzene / 3 h / Heating

2: 96 percent / H₂ / Pd/C / ethanol / 18 h / 2068.6 Torr / Ambient temperature

3: 90 percent / LiAlH₄ / diethyl ether / a) 0 deg C, 0.5 h, 2.) RT, 14 h

4: 1.) NaH, 2.) Bu₄NI / 1.) THF, 0 deg C, 20 min, 2.) THF, a) 0 deg C, 30 min, b) RT, 24 h

5: 60 percent / Dowex 50W-X₈ resin / methanol; H₂O / 24 h

6: 90 percent / 2,4,6-collidine / CH₂Cl₂ / 2 h / -78 °C

With 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; Dowex 50W-X₈ resin; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; water; benzene;
DOI:10.1139/v97-010