(1S,2R,8S,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol

Base Information

• Chemical Name: (1S,2R,8S,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol
• CAS No.: 105452-57-1
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.277
• Mol file: 105452-57-1.mol

Synonyms:

Chemical Property of (1S,2R,8S,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,8S,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol

There total 50 articles about (1S,2R,8S,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol 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%

(1(S),2(R),8(S),8a(S))-8-Hydroxy-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone (152185-81-4) → (1S,2R,8S,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol (85624-09-5,102208-65-1,105452-57-1,116497-18-8)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2012.06.006

Reference yield:

methyl 3-azido-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside (17460-38-7) → (1S,2R,8S,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol (85624-09-5,102208-65-1,105452-57-1,116497-18-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 5 min, 2.) RT, 1 h

2: 80percent aq. acetic acid / 4 h / 100 °C

3: concd. H₂SO₄ / 4 h / Ambient temperature

4: 82 percent / sodium methoxide / methanol / 0.08 h / Ambient temperature

5: 64 percent / pyridine, triethylamine / 6 h / Ambient temperature

6: 60 percent / benzene / 3 h / Heating

7: 88 percent / camphorsulfonic acid / acetone / 2 h / Ambient temperature

8: H₂ / Raney nickel W-4 / ethanol / 36 h / 760 Torr / Ambient temperature

9: Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

10: pyridine / 3 h / 40 °C

11: K₂CO₃ / dioxane; H₂O / 2 h / 90 °C

12: 64 percent / cyclohexene, 20percent Pd(OH)2/C / ethanol / 26 h / Heating

13: 83 percent / pyridine / 4 h / Ambient temperature

14: 84 percent / dimethylformamide / 0.5 h / 140 °C

15: BH₃-Me₂S / tetrahydrofuran / 2 h / Ambient temperature

16: K₂CO₃ / methanol / 2 h / 65 °C

With pyridine; palladium dihydroxide; dimethylsulfide borane complex; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; cyclohexene; Raney nickel W-4; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00257a003

Reference yield:

methyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside (39032-45-6) → (1S,2R,8S,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol (85624-09-5,102208-65-1,105452-57-1,116497-18-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 80percent aq. acetic acid / 4 h / 100 °C

2: concd. H₂SO₄ / 4 h / Ambient temperature

3: 82 percent / sodium methoxide / methanol / 0.08 h / Ambient temperature

4: 64 percent / pyridine, triethylamine / 6 h / Ambient temperature

5: 60 percent / benzene / 3 h / Heating

6: 88 percent / camphorsulfonic acid / acetone / 2 h / Ambient temperature

7: H₂ / Raney nickel W-4 / ethanol / 36 h / 760 Torr / Ambient temperature

8: Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

9: pyridine / 3 h / 40 °C

10: K₂CO₃ / dioxane; H₂O / 2 h / 90 °C

11: 64 percent / cyclohexene, 20percent Pd(OH)2/C / ethanol / 26 h / Heating

12: 83 percent / pyridine / 4 h / Ambient temperature

13: 84 percent / dimethylformamide / 0.5 h / 140 °C

14: BH₃-Me₂S / tetrahydrofuran / 2 h / Ambient temperature

15: K₂CO₃ / methanol / 2 h / 65 °C

With pyridine; palladium dihydroxide; dimethylsulfide borane complex; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; potassium carbonate; acetic acid; triethylamine; cyclohexene; Raney nickel W-4; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00257a003

upstream raw materials:

Benzoic acid (3aR,9S,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

(1(S),2(R),8(S),8a(S))-8-Hydroxy-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone

(S)-(-)-Tetrahydro-5-oxo-2-furancarboxaldehyde

(S)-(+)-Dihydro-5-<(E)-1,3-butadienyl>-2(3H)-furanone

Downstream raw materials:

(1S,2R,8S,8aS)-octahydro-1,2,8-indolizidinetriol