(2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

Base Information

Chemical Name:(2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide
CAS No.:944727-63-3
Molecular Formula:C₃₃H₃₈N₂O₆
Molecular Weight:558.675
Hs Code.:

Synonyms:(2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

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Chemical Property of (2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

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Technology Process of (2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

There total 10 articles about (2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide 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:

: 944727-62-2
(2S,3aR,5R,6S,7R,7aS)-6,7-di-O-benzyl-N'-methyl-octahydro-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

: 108-24-7
acetic anhydride

: 944727-63-3
(2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

Guidance literature:: With pyridine; at 20 ℃; for 15h;
DOI:10.1021/jo0700833

Reference yield:

: 944727-61-1
(2S,3aR,5R,6S,7R,7aS)-1-(tert-butyloxycarbonyl)-6,7-di-O-benzyl-N'-methyl-octahydro-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

: 944727-63-3
(2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

Guidance literature:: Multi-step reaction with 2 steps

1: 93.1 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

2: 0.030 g / pyridine / 15 h / 20 °C

With pyridine; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jo0700833

Reference yield:

: 944727-56-4
(2S,3aR,5R,6R,7S,7aS)-1-(tert-butyloxycarbonyl)-6,7-di-O-benzyl-2-(iodomethyl)-5-[(benzyloxy)methyl]octahydropyrano[3,2-b]pyrrole

: 944727-63-3
(2S,3aR,5R,6S,7R,7aS)-1-acetyloctahydro-6,7-di-O-benzyl-N'-methyl-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1: 92.1 percent / silver acetate / toluene / 16 h / 20 °C

2: 78.4 percent / potassium hydroxide / methanol / 4 h / Heating

3: 89.7 percent / triethylamine / methanol / 16 h / 20 °C

4: 78.4 percent / Jones reagent / acetone / 0.5 h / 0 °C

5: 84.3 percent / O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium BF₄; ethyldiisopropylamine / acetonitrile / 4 h / 20 °C

6: 93.1 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

7: 0.030 g / pyridine / 15 h / 20 °C

With pyridine; potassium hydroxide; jones reagent; silver(I) acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; acetone; toluene; acetonitrile; 4: Jones oxidation;
DOI:10.1021/jo0700833