(R)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid (1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl ester 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: (R)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid (1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl ester 2-trimethylsilanyl-ethyl ester
• CAS No.: 251353-66-9
• Molecular Formula: C₆₃H₈₉N₃O₁₀Si₂
• Molecular Weight: 1104.58

Synonyms:

Chemical Property of (R)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid (1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl ester 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid (1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl ester 2-trimethylsilanyl-ethyl ester

There total 22 articles about (R)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid (1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl ester 2-trimethylsilanyl-ethyl 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:

(2S,3R)-3-Benzyloxy-2-methyl-3-((S)-5-oxo-tetrahydro-furan-2-yl)-propionaldehyde → (R)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid (1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl ester 2-trimethylsilanyl-ethyl ester (251353-66-9)

Guidance literature:

Multi-step reaction with 12 steps

1: n-BuLi / tetrahydrofuran

2: H₂ / Pd-C / ethyl acetate

3: TfOH / CH₂Cl₂; cyclohexane

4: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

5: 72 percent / n-BuLi / diethyl ether / -20 °C

6: 85 percent / NaBH₄; CeCl₃ / methanol

7: 97 percent / Ac₂O; Py

8: 84 percent / Pd(OAc)2; n-Bu₃P / tetrahydrofuran

9: LiAlH₄ / tetrahydrofuran

10: PPTS / ethanol

11: 69 percent / HN₃; Ph₃P; DEAD / toluene

12: DMAP / toluene

With pyridine; dmap; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; tributylphosphine; tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; acetic anhydride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; ethyl acetate; toluene; 1: Condensation / 2: Catalytic hydrogenation / 3: Etherification / 4: Alkylation / 5: Acylation / 6: Reduction / 7: Esterification / 8: deoxygenation / 9: Reduction / 10: ether cleavage / 11: Alkylation / 12: Acylation;

DOI:10.1016/S0040-4039(99)01322-2

Reference yield:

(S)-5-((1R,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-dihydro-furan-2-one (251353-58-9) → (R)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid (1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl ester 2-trimethylsilanyl-ethyl ester (251353-66-9)

Guidance literature:

Multi-step reaction with 11 steps

1: H₂ / Pd-C / ethyl acetate

2: TfOH / CH₂Cl₂; cyclohexane

3: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

4: 72 percent / n-BuLi / diethyl ether / -20 °C

5: 85 percent / NaBH₄; CeCl₃ / methanol

6: 97 percent / Ac₂O; Py

7: 84 percent / Pd(OAc)2; n-Bu₃P / tetrahydrofuran

8: LiAlH₄ / tetrahydrofuran

9: PPTS / ethanol

10: 69 percent / HN₃; Ph₃P; DEAD / toluene

11: DMAP / toluene

With pyridine; dmap; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; tributylphosphine; tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; acetic anhydride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; ethyl acetate; toluene; 1: Catalytic hydrogenation / 2: Etherification / 3: Alkylation / 4: Acylation / 5: Reduction / 6: Esterification / 7: deoxygenation / 8: Reduction / 9: ether cleavage / 10: Alkylation / 11: Acylation;

DOI:10.1016/S0040-4039(99)01322-2

Reference yield:

(S)-5-((1R,2R)-1-Benzyloxy-3-hydroxy-2-methyl-propyl)-dihydro-furan-2-one (251353-68-1) → (R)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid (1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl ester 2-trimethylsilanyl-ethyl ester (251353-66-9)

Guidance literature:

Multi-step reaction with 13 steps

2: n-BuLi / tetrahydrofuran

3: H₂ / Pd-C / ethyl acetate

4: TfOH / CH₂Cl₂; cyclohexane

5: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

6: 72 percent / n-BuLi / diethyl ether / -20 °C

7: 85 percent / NaBH₄; CeCl₃ / methanol

8: 97 percent / Ac₂O; Py

9: 84 percent / Pd(OAc)2; n-Bu₃P / tetrahydrofuran

10: LiAlH₄ / tetrahydrofuran

11: PPTS / ethanol

12: 69 percent / HN₃; Ph₃P; DEAD / toluene

13: DMAP / toluene

With pyridine; dmap; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; tributylphosphine; tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; acetic anhydride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; ethyl acetate; toluene; 1: Oxidation / 2: Condensation / 3: Catalytic hydrogenation / 4: Etherification / 5: Alkylation / 6: Acylation / 7: Reduction / 8: Esterification / 9: deoxygenation / 10: Reduction / 11: ether cleavage / 12: Alkylation / 13: Acylation;

DOI:10.1016/S0040-4039(99)01322-2

upstream raw materials:

(3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-ol

(S)-5-((1R,2R)-1-Hydroxy-2-methyl-butyl)-dihydro-furan-2-one

(S)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid mono-(2-trimethylsilanyl-ethyl) ester

(S)-5-((1R,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-dihydro-furan-2-one

Downstream raw materials:

(R)-3-Carboxy-pentanedioic acid mono-[(1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl] ester

AAL-toxin TA₁

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