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

Base Information

Chemical Name:(2S,3aR,5R,6S,7R,7aS)-6,7-di-O-benzyl-N'-methyl-octahydro-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrole-2-carboxamide
CAS No.:944727-62-2
Molecular Formula:C₃₁H₃₆N₂O₅
Molecular Weight:516.637
Hs Code.:

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

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

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

There total 9 articles about (2S,3aR,5R,6S,7R,7aS)-6,7-di-O-benzyl-N'-methyl-octahydro-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: 93.1%

: 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

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

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo0700833

Reference yield:

: 944727-55-3
1-[2-(tert-butyloxycarbonylamino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl]-2-propene

: 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

Guidance literature:: Multi-step reaction with 7 steps

1: 89.6 percent / iodine / CH₂Cl₂; diethyl ether / 1 h / 0 °C

2: 92.1 percent / silver acetate / toluene / 16 h / 20 °C

3: 78.4 percent / potassium hydroxide / methanol / 4 h / Heating

4: 89.7 percent / triethylamine / methanol / 16 h / 20 °C

5: 78.4 percent / Jones reagent / acetone / 0.5 h / 0 °C

6: 84.3 percent / O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium BF₄; ethyldiisopropylamine / acetonitrile / 4 h / 20 °C

7: 93.1 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

With potassium hydroxide; jones reagent; iodine; silver(I) acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; acetone; toluene; acetonitrile; 5: Jones oxidation;
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

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

Guidance literature:: Multi-step reaction with 6 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

With 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