(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

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Chemical Name:(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester
CAS No.:871483-82-8
Molecular Formula:C₅₇H₆₅N₃O₁₁
Molecular Weight:968.157
Hs Code.:

(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

Synonyms:(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

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Chemical Property of (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

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Technology Process of (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

There total 17 articles about (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid 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: 84.0%

: 871483-79-3
(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-7-hydroxymethyl-5-isobutoxy-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester

: 645-45-4
hydrocinnamic acid chloride

: 871483-82-8
(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

Guidance literature:: With pyridine; In tetrahydrofuran;
DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

: (2R,3S)-2-Hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-ol

: 871483-82-8
(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 2,6-lutidine / -5 °C

2: 96 percent / (COCl)2; DMSO; Et₃N / -78 °C

3: 96 percent / I₂; pyridine / CH₂Cl₂

4: 67 percent / NaBH₄; CeCl₃*7H₂O / methanol

5: 57 percent / DIAD; PPh₃ / tetrahydrofuran / 20 °C

6: 72 percent / n-BuLi / tetrahydrofuran / -78 °C

7: 96 percent / NaBH₄; CeCl₃*7H₂O / methanol

8: 78 percent / (PPh₃)3RhCl; H₂

9: 92 percent / NaH / tetrahydrofuran

10: 90 percent / Na; naphthalene

11: 90 percent / K₂CO₃

12: aq. KOH / tetrahydrofuran / 0 °C

13: pyBOP; HOBt; DIPEA / CH₂Cl₂

14: 90 percent / HF*py / tetrahydrofuran / 20 °C

15: 84 percent / pyridine / tetrahydrofuran

With pyridine; 2,6-dimethylpyridine; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; naphthalene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; sodium; sodium hydride; potassium carbonate; benzotriazol-1-ol; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2: Swern oxidation / 4: Luche reduction / 5: Mitsunobu reaction / 7: Luche reduction;
DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

: Acetic acid (2R,3S)-2-acetoxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl ester

: 871483-82-8
(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: K₂CO₃; MeOH

2: 2,6-lutidine / -5 °C

3: 96 percent / (COCl)2; DMSO; Et₃N / -78 °C

4: 96 percent / I₂; pyridine / CH₂Cl₂

5: 67 percent / NaBH₄; CeCl₃*7H₂O / methanol

6: 57 percent / DIAD; PPh₃ / tetrahydrofuran / 20 °C

7: 72 percent / n-BuLi / tetrahydrofuran / -78 °C

8: 96 percent / NaBH₄; CeCl₃*7H₂O / methanol

9: 78 percent / (PPh₃)3RhCl; H₂

10: 92 percent / NaH / tetrahydrofuran

11: 90 percent / Na; naphthalene

12: 90 percent / K₂CO₃

13: aq. KOH / tetrahydrofuran / 0 °C

14: pyBOP; HOBt; DIPEA / CH₂Cl₂

15: 90 percent / HF*py / tetrahydrofuran / 20 °C

16: 84 percent / pyridine / tetrahydrofuran

With pyridine; 2,6-dimethylpyridine; methanol; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; naphthalene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; sodium; sodium hydride; potassium carbonate; benzotriazol-1-ol; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 3: Swern oxidation / 5: Luche reduction / 6: Mitsunobu reaction / 8: Luche reduction;
DOI:10.1016/j.bmcl.2005.08.062