(1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol

Base Information

Chemical Name:(1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol
CAS No.:312515-07-4
Molecular Formula:C₂₂H₂₇NO₄
Molecular Weight:369.461
Hs Code.:

Synonyms:

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Chemical Property of (1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol

Chemical Property:

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Technology Process of (1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol

There total 25 articles about (1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol 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:

: Toluene-4-sulfonic acid (S)-3-((2S,3R,4S,5R)-3,4-bis-benzyloxy-5-methoxymethoxy-pyrrolidin-2-yl)-3-methoxymethoxy-propyl ester

: 312515-07-4
(1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol

Guidance literature:: With potassium carbonate; In methanol;
DOI:10.1016/S0040-4039(00)01314-9

Reference yield:

: 160549-10-0
2,3,5-tri-O-benzyl-D-arabinofuranose

: 312515-07-4
(1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol

Guidance literature:: Multi-step reaction with 25 steps

1: 100 percent / MS 4 Angstroem / benzene; CHCl₃ / reflux

2: 70 percent / tetrahydrofuran / -78 - -40 °C

3: 68 percent / PCC; MS 4 Angstroem / CH₂Cl₂

4: 98 percent / OsO₄; NMO / acetone; H₂O

5: NaIO₄ / diethyl ether; H₂O

6: BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

7: 71 percent / CAN / acetonitrile; H₂O

8: 75 percent / (i-Pr)2NEt / CH₂Cl₂

9: 91 percent / OsO₄; NMO / acetone; H₂O

10: NaIO₄ / diethyl ether; H₂O

11: NaBH₄ / ethanol

12: 100 percent / imidazole / dimethylformamide

13: 99 percent / Et₃N; DMAP / CH₂Cl₂

14: tetrahydrofuran / -78 °C

15: NaBH₄; CeCl₃ / methanol / -45 °C

16: Et₃N / CH₂Cl₂

17: t-BuOK / tetrahydrofuran

18: 92 percent / OsO₄; NMO / acetone; H₂O

19: NaIO₄ / diethyl ether; H₂O

20: NaBH₄ / ethanol

21: 99 percent / (i-Pr)2NEt / CH₂Cl₂

22: 100 percent / Bu₄NF / tetrahydrofuran

23: 92 percent / pyridine

24: conc. HCl / methanol

25: K₂CO₃ / methanol

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; ammonium cerium(IV) nitrate; MS 4 Angstroem; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 1: Condensation / 2: Addition / 3: Oxidation / 4: Oxidation / 5: Oxidation / 6: Addition / 7: Oxidation / 8: Etherification / 9: Oxidation / 10: Oxidation / 11: Reduction / 12: Etherification / 13: Acylation / 14: Addition / 15: Reduction / 16: Acylation / 17: Cyclization / 18: Oxidation / 19: Oxidation / 20: Reduction / 21: Etherification / 22: desilylation / 23: Tosylation / 24: deacylation / 25: Cyclization;
DOI:10.1016/S0040-4039(00)01314-9

Reference yield:

: 157831-26-0
(3S,4R,5S)-3,4-dibenzyloxy-1-(4-methoxyphenylmethyl)-5-vinylpyrrolidin-2-one

: 312515-07-4
(1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol

Guidance literature:: Multi-step reaction with 22 steps

1: 98 percent / OsO₄; NMO / acetone; H₂O

2: NaIO₄ / diethyl ether; H₂O

3: BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

4: 71 percent / CAN / acetonitrile; H₂O

5: 75 percent / (i-Pr)2NEt / CH₂Cl₂

6: 91 percent / OsO₄; NMO / acetone; H₂O

7: NaIO₄ / diethyl ether; H₂O

8: NaBH₄ / ethanol

9: 100 percent / imidazole / dimethylformamide

10: 99 percent / Et₃N; DMAP / CH₂Cl₂

11: tetrahydrofuran / -78 °C

12: NaBH₄; CeCl₃ / methanol / -45 °C

13: Et₃N / CH₂Cl₂

14: t-BuOK / tetrahydrofuran

15: 92 percent / OsO₄; NMO / acetone; H₂O

16: NaIO₄ / diethyl ether; H₂O

17: NaBH₄ / ethanol

18: 99 percent / (i-Pr)2NEt / CH₂Cl₂

19: 100 percent / Bu₄NF / tetrahydrofuran

20: 92 percent / pyridine

21: conc. HCl / methanol

22: K₂CO₃ / methanol

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 1: Oxidation / 2: Oxidation / 3: Addition / 4: Oxidation / 5: Etherification / 6: Oxidation / 7: Oxidation / 8: Reduction / 9: Etherification / 10: Acylation / 11: Addition / 12: Reduction / 13: Acylation / 14: Cyclization / 15: Oxidation / 16: Oxidation / 17: Reduction / 18: Etherification / 19: desilylation / 20: Tosylation / 21: deacylation / 22: Cyclization;
DOI:10.1016/S0040-4039(00)01314-9