<(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

Base Information

Chemical Name:<(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester
CAS No.:124562-30-7
Molecular Formula:C₄₆H₇₅N₇O₉
Molecular Weight:870.143
Hs Code.:

<(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

Synonyms:<(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

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Chemical Property of <(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

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Technology Process of <(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

There total 14 articles about <(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester 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:

: 124562-28-3
C₄₉H₇₉N₇O₉

: 124562-30-7
<(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

Guidance literature:: With hydrogenchloride; In methanol; for 48h; Yield given; Ambient temperature;
DOI:10.1021/jm00165a018

Reference yield:

: 26817-34-5
hepta-2,5-diyn-1-ol

: 124562-30-7
<(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: LiAlH₄ / diethyl ether / 7 h / Heating

2: 74 percent / 4-Angstroem sieves, diethyl L-tartrate, titanium tetraisopropoxide, 3N tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 1.) -10 to 0 deg C, 4 h, 2.) -20 deg C, overnight

3: 93 percent / DBU / CH₂Cl₂ / 36 h / Ambient temperature

4: 27 percent / CuI, BF₃*Et₂O, MeLi / tetrahydrofuran; diethyl ether / 2 h / -30 - 0 °C

5: 2.) TsOH*H₂O / 1.) toluene, 110 deg C, 7 h, 2.) methanol, ether, RT, 38 h

6: 67 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1 h / -40 - 20 °C

7: 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 2 h

8: BF₃*Et₂O / nitromethane / 1 h / Ambient temperature

9: 1.) K₂CO₃, H₂O, 2.) 2N HCl / 1.) aq. ethanol, 9 h, 2.) RT, 6h

10: 90 percent / 2N NaOH / methanol / 2 h / Ambient temperature

11: 75 mg / 2N KOH, Dowex H⁺ / 5 h / Heating

12: 24 h / Heating

13: N-methylmorpholine, N-hydroxybenzotriazole, DCC / tetrahydrofuran / 1.) 0 deg C, 0.5 h, 2.) RT, 26 h

14: 1N HCl / methanol / 48 h / Ambient temperature

With 4-methyl-morpholine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; potassium hydroxide; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; Dowex H⁺; boron trifluoride diethyl etherate; water; methyllithium; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; nitromethane; dichloromethane;
DOI:10.1021/jm00165a018

Reference yield:

: 124562-11-4
(E)-hept-2-en-5-yn-1-ol

: 124562-30-7
<(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 74 percent / 4-Angstroem sieves, diethyl L-tartrate, titanium tetraisopropoxide, 3N tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 1.) -10 to 0 deg C, 4 h, 2.) -20 deg C, overnight

2: 93 percent / DBU / CH₂Cl₂ / 36 h / Ambient temperature

3: 27 percent / CuI, BF₃*Et₂O, MeLi / tetrahydrofuran; diethyl ether / 2 h / -30 - 0 °C

4: 2.) TsOH*H₂O / 1.) toluene, 110 deg C, 7 h, 2.) methanol, ether, RT, 38 h

5: 67 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1 h / -40 - 20 °C

6: 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 2 h

7: BF₃*Et₂O / nitromethane / 1 h / Ambient temperature

8: 1.) K₂CO₃, H₂O, 2.) 2N HCl / 1.) aq. ethanol, 9 h, 2.) RT, 6h

9: 90 percent / 2N NaOH / methanol / 2 h / Ambient temperature

10: 75 mg / 2N KOH, Dowex H⁺ / 5 h / Heating

11: 24 h / Heating

12: N-methylmorpholine, N-hydroxybenzotriazole, DCC / tetrahydrofuran / 1.) 0 deg C, 0.5 h, 2.) RT, 26 h

13: 1N HCl / methanol / 48 h / Ambient temperature

With 4-methyl-morpholine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; potassium hydroxide; sodium hydroxide; copper(l) iodide; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; Dowex H⁺; boron trifluoride diethyl etherate; water; methyllithium; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; nitromethane; dichloromethane;
DOI:10.1021/jm00165a018