(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

Base Information

Chemical Name:(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
CAS No.:944727-61-1
Molecular Formula:C₃₆H₄₄N₂O₇
Molecular Weight:616.755
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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: 84.3%

: 944727-54-2
(2S,3aR,5R,6R,7S,7aS)-1-(tert-butyloxycarbonyl)-6,7-di-O-benzyl-5-[(benzyloxy)methyl]octahydropyrano[3,2-b]pyrrole-2-carboxylic acid

: 593-51-1
methylamine hydrochloride

: 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

Guidance literature:: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 4h;
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

: 944727-61-1
(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

Guidance literature:: Multi-step reaction with 6 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

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; In methanol; diethyl ether; dichloromethane; acetone; toluene; acetonitrile; 5: Jones oxidation;
DOI:10.1021/jo0700833

Reference yield:

: 944727-57-5
(2S,3aR,5R,6S,7R,7aS)-1-(tert-butyloxycarbonyl)-6,7-di-O-benzyl-octahydro-5-(phenylmethyloxymethyl)-pyrano[3,2-b]pyrrolo[1,2-c]-oxazol-3-one

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: 78.4 percent / potassium hydroxide / methanol / 4 h / Heating

2: 89.7 percent / triethylamine / methanol / 16 h / 20 °C

3: 78.4 percent / Jones reagent / acetone / 0.5 h / 0 °C

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

With potassium hydroxide; jones reagent; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; acetone; acetonitrile; 3: Jones oxidation;
DOI:10.1021/jo0700833