Methyl of N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate

Base Information

• Chemical Name: Methyl of N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate
• CAS No.: 108071-98-3
• Molecular Formula: C₄₀H₅₅ClN₄O₉
• Molecular Weight: 771.351
• Mol file: 108071-98-3.mol

Synonyms:

Chemical Property of Methyl of N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl of N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate

There total 13 articles about Methyl of N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate 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:

Methyl 10-Benzyloxy-2-(S)-benzyloxycarbonylamino-8(S),9(S)-O-isopropylidene-2(E/Z),6(E/Z)-decadienoate (89278-31-9) → Methyl of N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate (108071-98-3)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / +BF₄- / ethanol / 72 h / 2250.2 Torr / Ambient temperature

2: H₂ / Pd / methanol / 24 h / 2250.2 Torr / Ambient temperature

4: 1-chlor-1-dimethylamino-2-methyl-1-propen, pyridine / CH₂Cl₂ / 1.) -20 deg C, 30 min 2.) 40 deg C, 30 min

5: NaOH pH<11 / H₂O; dioxane / 5 h / Ambient temperature

6: DCCD / ethyl acetate / -20 deg C to RT

With pyridine; sodium hydroxide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; hydrogen; dicyclohexyl-carbodiimide; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; palladium; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate;

Reference yield:

8-Benzyloxy-6(S),7(S)-O-isopropylidene-1-octanal (89278-34-2) → Methyl of N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate (108071-98-3)

Guidance literature:

Multi-step reaction with 7 steps

1: KO-tBu / CH₂Cl₂ / 0.5 h / -70 °C

2: H₂ / +BF₄- / ethanol / 72 h / 2250.2 Torr / Ambient temperature

3: H₂ / Pd / methanol / 24 h / 2250.2 Torr / Ambient temperature

5: 1-chlor-1-dimethylamino-2-methyl-1-propen, pyridine / CH₂Cl₂ / 1.) -20 deg C, 30 min 2.) 40 deg C, 30 min

6: NaOH pH<11 / H₂O; dioxane / 5 h / Ambient temperature

7: DCCD / ethyl acetate / -20 deg C to RT

With pyridine; sodium hydroxide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; potassium tert-butylate; hydrogen; dicyclohexyl-carbodiimide; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; palladium; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate;

Reference yield:

(4S,5S)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester (78513-04-9) → Methyl of N-<2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoyl>-dimethylglycyl-(S)-phenylalanyl-(R)-prolinate (108071-98-3)

Guidance literature:

Multi-step reaction with 8 steps

2: KO-tBu / CH₂Cl₂ / 0.5 h / -70 °C

3: H₂ / +BF₄- / ethanol / 72 h / 2250.2 Torr / Ambient temperature

4: H₂ / Pd / methanol / 24 h / 2250.2 Torr / Ambient temperature

6: 1-chlor-1-dimethylamino-2-methyl-1-propen, pyridine / CH₂Cl₂ / 1.) -20 deg C, 30 min 2.) 40 deg C, 30 min

7: NaOH pH<11 / H₂O; dioxane / 5 h / Ambient temperature

8: DCCD / ethyl acetate / -20 deg C to RT

With pyridine; sodium hydroxide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; potassium tert-butylate; hydrogen; dicyclohexyl-carbodiimide; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; palladium; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate;

upstream raw materials:

Methyl 2(S)-benzyloxycarbonylamino-10-chloro-8(S),9(R)-O-isopropylidenedecanoate

Methyl N-(dimethylglycyl)-(S)-phenylalanyl-(R)-prolinate

(S)-2-Benzyloxycarbonylamino-7-((4S,5R)-5-chloromethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptanoic acid

8-Benzyloxy-6(S),7(S)-O-isopropylidene-1-octanal

Downstream raw materials:

cyclo<(2(γ)-Amino-10-chloro-8(S),9(R)-dihydroxydecanoyl)-dimethylglycyl-(S)-phenylalanyl-(R)-prolyl>

chlamydocin

chlamydocin

Dihydrochlamydocin