(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid

Base Information

Chemical Name:(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid
CAS No.:450371-26-3
Molecular Formula:C₅₃H₆₂N₂O₁₀
Molecular Weight:887.083
Hs Code.:

(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid

Synonyms:(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid

There total 12 articles about (S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic 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: 85.0%

: 450371-24-1
((S)-1-{(S)-3-((1R,2R,4R)-2-Hydroxy-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-3-oxo-1-[2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-propylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

: 464-49-3,68546-28-1
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

: 450371-26-3
(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid

Guidance literature:: With ammonium cerium(IV) nitrate; In acetonitrile; at 0 ℃; for 0.25h;
DOI:10.1021/ja026250s

Reference yield:

: 3879-79-6,17791-37-6,19488-61-0,53008-63-2,61330-62-9,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2
methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

: 450371-26-3
(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 20 °C

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 16 h / 65 °C

2.2: H₂O₂; aq. NaOH / 1 / 1 h / 55 °C

3.1: 1,1,1,3,3,3-hexachloro-propan-2-one; dimethyl sulfoxide; triethylamine / dichloromethane / 0.08 h / -78 °C

4.1: formic acid / tetrahydrofuran / 16 h

5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.42 h / -78 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7.1: ammonium acetate; hydrogen / palladium on activated charcoal / methanol / 20 °C / 760.05 Torr

8.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 17 h / 0 - 20 °C

9.1: ammonium cerium(IV) nitrate / acetonitrile / 0.25 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; formic acid; ammonium cerium(IV) nitrate; 1,1,1,3,3,3-hexachloro-propan-2-one; trimethylsilyl trifluoromethanesulfonate; ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; 3.1: Swern oxidation / 5.1: Mannich reaction;
DOI:10.1021/ja026250s

Reference yield:

: 82659-52-7
1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene

: 450371-26-3
(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 16 h / 65 °C

1.2: H₂O₂; aq. NaOH / 1 / 1 h / 55 °C

2.1: 1,1,1,3,3,3-hexachloro-propan-2-one; dimethyl sulfoxide; triethylamine / dichloromethane / 0.08 h / -78 °C

3.1: formic acid / tetrahydrofuran / 16 h

4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.42 h / -78 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C

7.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 17 h / 0 - 20 °C

8.1: ammonium cerium(IV) nitrate / acetonitrile / 0.25 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; formic acid; ammonium cerium(IV) nitrate; 1,1,1,3,3,3-hexachloro-propan-2-one; tetrabutyl ammonium fluoride; benzotriazol-1-ol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 2.1: Swern oxidation / 4.1: Mannich reaction;
DOI:10.1021/ja026250s