(1R,2R,3S,4R)-3-Benzyloxy-1-tert-butyldiphenylsilyloxy-4-ethoxycarbonylmethyl-2-formyloxycyclopentane

Base Information

Chemical Name:(1R,2R,3S,4R)-3-Benzyloxy-1-tert-butyldiphenylsilyloxy-4-ethoxycarbonylmethyl-2-formyloxycyclopentane
CAS No.:145741-61-3
Molecular Formula:C₃₃H₄₀O₆Si
Molecular Weight:560.763
Hs Code.:

Synonyms:

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Chemical Property of (1R,2R,3S,4R)-3-Benzyloxy-1-tert-butyldiphenylsilyloxy-4-ethoxycarbonylmethyl-2-formyloxycyclopentane

Chemical Property:

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Technology Process of (1R,2R,3S,4R)-3-Benzyloxy-1-tert-butyldiphenylsilyloxy-4-ethoxycarbonylmethyl-2-formyloxycyclopentane

There total 9 articles about (1R,2R,3S,4R)-3-Benzyloxy-1-tert-butyldiphenylsilyloxy-4-ethoxycarbonylmethyl-2-formyloxycyclopentane 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:

: 14686-89-6
(1,2:5,6)-di-O-isopropylidene-D-gulose

: 145741-61-3
(1R,2R,3S,4R)-3-Benzyloxy-1-tert-butyldiphenylsilyloxy-4-ethoxycarbonylmethyl-2-formyloxycyclopentane

Guidance literature:: Multi-step reaction with 8 steps

1: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, r.t., 45 min, 2) reflux, 1 h

2: conc. HCl / H₂O; methanol / 23 h / Ambient temperature

3: 71 percent / CBr₄, triphenylphosphine, pyridine / 0.15 h / 60 °C

4: 85 percent / imidazole, DMAP / CH₂Cl₂ / 17 h / Ambient temperature

5: 96 percent / 80percent aq AcOH / 15.5 h / 65 °C

6: 2.11 g / sodium metaperiodate / H₂O; methanol / 2.5 h / Ambient temperature

7: 72 percent / benzoic acid / benzene / 15 h / Ambient temperature

8: tributyltin hydride, azosobutyronitrile / benzene / 9 h / Heating

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium periodate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triphenylphosphine; benzoic acid; In methanol; dichloromethane; water; benzene;
DOI:10.1039/P19920002625

Reference yield:

: 57099-04-4
3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

: 145741-61-3
(1R,2R,3S,4R)-3-Benzyloxy-1-tert-butyldiphenylsilyloxy-4-ethoxycarbonylmethyl-2-formyloxycyclopentane

Guidance literature:: Multi-step reaction with 6 steps

1: 71 percent / CBr₄, triphenylphosphine, pyridine / 0.15 h / 60 °C

2: 85 percent / imidazole, DMAP / CH₂Cl₂ / 17 h / Ambient temperature

3: 96 percent / 80percent aq AcOH / 15.5 h / 65 °C

4: 2.11 g / sodium metaperiodate / H₂O; methanol / 2.5 h / Ambient temperature

5: 72 percent / benzoic acid / benzene / 15 h / Ambient temperature

6: tributyltin hydride, azosobutyronitrile / benzene / 9 h / Heating

With pyridine; 1H-imidazole; dmap; sodium periodate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tri-n-butyl-tin hydride; acetic acid; triphenylphosphine; benzoic acid; In methanol; dichloromethane; water; benzene;
DOI:10.1039/P19920002625

Reference yield:

: 22331-21-1
1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

: 145741-61-3
(1R,2R,3S,4R)-3-Benzyloxy-1-tert-butyldiphenylsilyloxy-4-ethoxycarbonylmethyl-2-formyloxycyclopentane

Guidance literature:: Multi-step reaction with 7 steps

1: conc. HCl / H₂O; methanol / 23 h / Ambient temperature

2: 71 percent / CBr₄, triphenylphosphine, pyridine / 0.15 h / 60 °C

3: 85 percent / imidazole, DMAP / CH₂Cl₂ / 17 h / Ambient temperature

4: 96 percent / 80percent aq AcOH / 15.5 h / 65 °C

5: 2.11 g / sodium metaperiodate / H₂O; methanol / 2.5 h / Ambient temperature

6: 72 percent / benzoic acid / benzene / 15 h / Ambient temperature

7: tributyltin hydride, azosobutyronitrile / benzene / 9 h / Heating

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium periodate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tri-n-butyl-tin hydride; acetic acid; triphenylphosphine; benzoic acid; In methanol; dichloromethane; water; benzene;
DOI:10.1039/P19920002625