(3R,3aS,4S,6aS)-3a-Hydroxy-4-((E)-(2R,3R)-3-hydroxy-5-iodo-2-methyl-pent-4-enyl)-6a-hydroxymethyl-1,3-dimethyl-tetrahydro-furo[3,4-b]pyrrole-2,6-dione

Base Information

Chemical Name:(3R,3aS,4S,6aS)-3a-Hydroxy-4-((E)-(2R,3R)-3-hydroxy-5-iodo-2-methyl-pent-4-enyl)-6a-hydroxymethyl-1,3-dimethyl-tetrahydro-furo[3,4-b]pyrrole-2,6-dione
CAS No.:127232-56-8
Molecular Formula:C₁₅H₂₂INO₆
Molecular Weight:439.247
Hs Code.:

(3R,3aS,4S,6aS)-3a-Hydroxy-4-((E)-(2R,3R)-3-hydroxy-5-iodo-2-methyl-pent-4-enyl)-6a-hydroxymethyl-1,3-dimethyl-tetrahydro-furo[3,4-b]pyrrole-2,6-dione

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Chemical Property of (3R,3aS,4S,6aS)-3a-Hydroxy-4-((E)-(2R,3R)-3-hydroxy-5-iodo-2-methyl-pent-4-enyl)-6a-hydroxymethyl-1,3-dimethyl-tetrahydro-furo[3,4-b]pyrrole-2,6-dione

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Technology Process of (3R,3aS,4S,6aS)-3a-Hydroxy-4-((E)-(2R,3R)-3-hydroxy-5-iodo-2-methyl-pent-4-enyl)-6a-hydroxymethyl-1,3-dimethyl-tetrahydro-furo[3,4-b]pyrrole-2,6-dione

There total 2 articles about (3R,3aS,4S,6aS)-3a-Hydroxy-4-((E)-(2R,3R)-3-hydroxy-5-iodo-2-methyl-pent-4-enyl)-6a-hydroxymethyl-1,3-dimethyl-tetrahydro-furo[3,4-b]pyrrole-2,6-dione 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: 100.0%

: 127232-55-7
(3R,3aS,4S,6aS)-4-[(E)-(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-2-methyl-pent-4-enyl]-6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-hydroxy-1,3-dimethyl-tetrahydro-furo[3,4-b]pyrrole-2,6-dione

: 127232-56-8
(3R,3aS,4S,6aS)-3a-Hydroxy-4-((E)-(2R,3R)-3-hydroxy-5-iodo-2-methyl-pent-4-enyl)-6a-hydroxymethyl-1,3-dimethyl-tetrahydro-furo[3,4-b]pyrrole-2,6-dione

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃;
DOI:10.1021/ja00166a072

Reference yield:

: 5540-26-1
3,4-Anhydro-6-O-benzyl-α-D-methyl-galactosid

: 127232-56-8
(3R,3aS,4S,6aS)-3a-Hydroxy-4-((E)-(2R,3R)-3-hydroxy-5-iodo-2-methyl-pent-4-enyl)-6a-hydroxymethyl-1,3-dimethyl-tetrahydro-furo[3,4-b]pyrrole-2,6-dione

Guidance literature:: Multi-step reaction with 17 steps

1: 95 percent / tetrahydrofuran; diethyl ether / 16 h / 23 °C

2: 2,6-lutidine / tetrahydrofuran / 16 h / -78 - 23 °C

3: 1.) S=C(Im)2, 2.) n-Bu₃SnH / 1.) CH₂Cl₂, reflux, 2.) xylene, reflux, 6 h

4: n-Bu₄NF / tetrahydrofuran / 23 °C

5: FeCl₃ / 4 h / 23 °C

6: H₂ / Pd(OH)2 / methanol / 4 h / 23 °C

7: 1.) (COCl)2, DMSO, Et₃N, 2.) KMnO₄, 5percent NaH₂PO₄ / 1.) CH₂Cl₂, a.) -78 deg C, 20 min, b.) 0 deg C 1 h, 2.) t-BuOH, 23 deg C, 0.5 h

8: diethyl ether / 0 °C

9: 1.) t-BuLi, TMEDA / 1.) THF, -78 deg C, 2.) -78 deg C

10: 100 percent / concd. HCl

11: 2,6-lutidine / CH₂Cl₂ / 23 °C

12: LiOH / tetrahydrofuran; H₂O / 1 h / 23 °C

13: 1.) 2N=CHCl>Cl, 2.) NaBH₄ / 1.) acetonitrile, THF, 0 deg C, 1 h, 2.) DMF, -78 deg C to 23 deg C, 16 h

14: 2,6-lutidine / CH₂Cl₂ / 0 °C

15: 99 percent / HgCl₂, CaCO₃ / acetonitrile; H₂O / 1 h / 23 °C

16: 70 percent / CrCl₂ / tetrahydrofuran / 1.5 h / 23 °C

17: 100 percent / n-Bu₄NF / tetrahydrofuran / 23 °C

With 2,6-dimethylpyridine; chromium dichloride; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; potassium permanganate; sodium dihydrogenphosphate; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; Vilsmeier reagent; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; tri-n-butyl-tin hydride; iron(III) chloride; dimethyl sulfoxide; triethylamine; 1,1'-Thiocarbonyldiimidazole; calcium carbonate; mercury dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/ja00166a072