(2S,6R)-7-(benzyloxy)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-7-oxoheptanoic acid

Base Information

• Chemical Name: (2S,6R)-7-(benzyloxy)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-7-oxoheptanoic acid
• CAS No.: 1104583-44-9
• Molecular Formula: C₂₇H₃₄N₂O₈
• Molecular Weight: 514.576

Synonyms:(2S,6R)-7-(benzyloxy)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-7-oxoheptanoic acid

Chemical Property of (2S,6R)-7-(benzyloxy)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-7-oxoheptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6R)-7-(benzyloxy)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-7-oxoheptanoic acid

There total 9 articles about (2S,6R)-7-(benzyloxy)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-7-oxoheptanoic acid 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: 86.0%

benzyl (2R,6S)-2-(benzyloxycarbonylamino)-6-(tert-butoxycarbonylamino)-7-hydroxyheptanoate (1104583-42-7) → (2S,6R)-7-(benzyloxy)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-7-oxoheptanoic acid (1104583-44-9)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; for 24h; Inert atmosphere;

DOI:10.1002/chem.200801121

Reference yield:

(R)-benzyl 2-(((benzyloxy)carbonyl)amino)pent-4-enoate (167466-67-3) → (2S,6R)-7-(benzyloxy)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-7-oxoheptanoic acid (1104583-44-9)

Guidance literature:

Multi-step reaction with 4 steps

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

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; toluene-4-sulfonic acid; In methanol; aq. phosphate buffer; water; ethyl acetate; toluene; acetonitrile; 1: |Cross Metathesis;

DOI:10.3390/molecules18011162

Reference yield:

tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (133625-87-3) → (2S,6R)-7-(benzyloxy)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-7-oxoheptanoic acid (1104583-44-9)

Guidance literature:

Multi-step reaction with 4 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

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; toluene-4-sulfonic acid; In methanol; aq. phosphate buffer; dichloromethane; water; ethyl acetate; acetonitrile; 1: |Cross Metathesis;

DOI:10.3390/molecules18011162

upstream raw materials:

benzyl (2R,6S)-2-(benzyloxycarbonylamino)-6-(tert-butoxycarbonylamino)-7-hydroxyheptanoate

tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate

(1'Z)-tert-butyl (4S)-2,2-dimethyl-4-(1'-propenyl)-3-oxazolidinecarboxylate

(S)-(tert-butyl) 2,2-dimethyl-4-styryloxazolidine-3-carboxylate

Downstream raw materials:

C₃₇H₄₅N₃O₉

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

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

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

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