(2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate

Base Information

Chemical Name:(2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate
CAS No.:1423076-23-6
Molecular Formula:C₄₁H₄₅N₃O₉
Molecular Weight:723.823
Hs Code.:

Synonyms:(2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate

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Chemical Property of (2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate

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Technology Process of (2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate

There total 9 articles about (2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate 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: 72.0%

: 1423076-22-5
(2S,6R)-dibenzyl 2-((R)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate

: 1423076-23-6
(2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate

Guidance literature:: With diethylamine; In tetrahydrofuran; at 20 ℃; for 3h; Cooling with ice;
DOI:10.3390/molecules18011162

Reference yield:

: 167466-67-3
(R)-benzyl 2-(((benzyloxy)carbonyl)amino)pent-4-enoate

: 1423076-23-6
(2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate

Guidance literature:: Multi-step reaction with 8 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 7 h / Reflux

2: platinum(IV) oxide; hydrogen / ethyl acetate / 14 h / 20 °C

3: toluene-4-sulfonic acid / methanol; water / 36 h / 20 °C

4: 2,2,6,6-tetramethylpiperidin-1-ol; sodium chlorite; sodium hypochlorite / water; aq. phosphate buffer; acetonitrile / 18.5 h / 40 °C / pH 6.5

5: 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline / dichloromethane / 19 h / 20 °C

6: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

7: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20.33 h / -20 - 20 °C

8: diethylamine / tetrahydrofuran / 3 h / 20 °C / Cooling with ice

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; platinum(IV) oxide; sodium hypochlorite; sodium chlorite; 2,2,6,6-tetramethylpiperidin-1-ol; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; triethylamine; trifluoroacetic acid; 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline; In tetrahydrofuran; methanol; aq. phosphate buffer; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: |Cross Metathesis;
DOI:10.3390/molecules18011162

Reference yield:

: 1423076-21-4
(S)-(tert-butyl) 4-((R)-5-(benzyloxy)-4-(benzyloxycarbonylamino)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1423076-23-6
(2S,6R)-dibenzyl 2-((R)-4-amino-5-(benzyloxy)-5-oxopentanamido)-6-(benzyloxycarbonylamino)heptanedioate

Guidance literature:: Multi-step reaction with 6 steps

1: toluene-4-sulfonic acid / methanol; water / 36 h / 20 °C

2: 2,2,6,6-tetramethylpiperidin-1-ol; sodium chlorite; sodium hypochlorite / water; aq. phosphate buffer; acetonitrile / 18.5 h / 40 °C / pH 6.5

3: 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline / dichloromethane / 19 h / 20 °C

4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

5: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20.33 h / -20 - 20 °C

6: diethylamine / tetrahydrofuran / 3 h / 20 °C / Cooling with ice

With sodium hypochlorite; sodium chlorite; 2,2,6,6-tetramethylpiperidin-1-ol; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; triethylamine; trifluoroacetic acid; 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline; In tetrahydrofuran; methanol; aq. phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.3390/molecules18011162