(S)-3-Benzyloxycarbonylamino-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid

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Chemical Name:(S)-3-Benzyloxycarbonylamino-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid
CAS No.:450370-81-7
Molecular Formula:C₄₇H₅₁NO₉
Molecular Weight:773.923
Hs Code.:

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

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

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

There total 7 articles about (S)-3-Benzyloxycarbonylamino-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: 88.0%

: 450370-62-4
{(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]-propyl}-carbamic acid benzyl ester

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

: 450370-81-7
(S)-3-Benzyloxycarbonylamino-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

: 450370-81-7
(S)-3-Benzyloxycarbonylamino-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 7 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 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; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 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

: 450370-81-7
(S)-3-Benzyloxycarbonylamino-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 6 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: 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; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 2.1: Swern oxidation / 4.1: Mannich reaction;
DOI:10.1021/ja026250s