{(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 tert-butyl ester

Base Information

Chemical Name:{(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 tert-butyl ester
CAS No.:450370-77-1
Molecular Formula:C₅₄H₆₉NO₉
Molecular Weight:876.143
Hs Code.:

{(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 tert-butyl ester

Synonyms:{(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 tert-butyl ester

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Chemical Property of {(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 tert-butyl ester

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Technology Process of {(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 tert-butyl ester

There total 10 articles about {(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 tert-butyl 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: 82.0%

: {(S)-3-Oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-1-[2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-propyl}-carbamic acid tert-butyl ester

: 450370-77-1
{(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]-propyl}-carbamic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
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

: 450370-77-1
{(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]-propyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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

With 9-borabicyclo[3.3.1]nonane dimer; formic acid; 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:

: 1075216-42-0
2-ethinyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

: 450370-77-1
{(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]-propyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: sulfuric acid; mercury(II) oxide / water; acetone / 0.25 h / 60 °C

2: potassium hydride / tetrahydrofuran / 1 h / 20 °C

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

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

With sulfuric acid; tetrabutyl ammonium fluoride; potassium hydride; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; water; acetone; 3: Mannich reaction;
DOI:10.1021/ja026250s