1-((2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)cyclopropanol

Base Information

Chemical Name:1-((2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)cyclopropanol
CAS No.:1270018-14-8
Molecular Formula:C₄₃H₄₀ClNO₆S
Molecular Weight:734.313
Hs Code.:

Synonyms:1-((2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)cyclopropanol

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Chemical Property of 1-((2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)cyclopropanol

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Technology Process of 1-((2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)cyclopropanol

There total 6 articles about 1-((2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)cyclopropanol 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: 56.0%

: 1270018-10-4
(2S,3S,4R,5S,6S)-methyl 3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-carboxylate

: 2386-64-3
ethylmagnesium chloride

: 1270018-14-8
1-((2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)cyclopropanol

Guidance literature:: With titanium(IV) isopropylate; In tetrahydrofuran; at 0 ℃; for 3h;
DOI:10.1016/j.bmcl.2010.11.115

Reference yield:

: 1270017-94-1
C₄₈H₄₄ClNO₆S

: 1270018-14-8
1-((2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)cyclopropanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: trimethylsilyl trifluoromethanesulfonate; acetic anhydride / dichloromethane / 1 h / -55 °C

1.2: 2 h / 20 °C

2.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

3.1: sodium chlorite; potassium dihydrogenphosphate / 2-methyl-but-2-ene; water; tert-butyl alcohol / 15 h / 20 °C

4.1: dichloromethane / 15 h / 0 - 20 °C

5.1: titanium(IV) isopropylate / tetrahydrofuran / 3 h / 0 °C

With titanium(IV) isopropylate; sodium chlorite; potassium dihydrogenphosphate; trimethylsilyl trifluoromethanesulfonate; acetic anhydride; Dess-Martin periodane; In tetrahydrofuran; 2-methyl-but-2-ene; dichloromethane; water; tert-butyl alcohol; 5.1: Kulinkovich cyclopropanation;
DOI:10.1016/j.bmcl.2010.11.115

Reference yield:

: 1270017-98-5
(2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-carbaldehyde

: 1270018-14-8
1-((2S,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)cyclopropanol

Guidance literature:: Multi-step reaction with 3 steps

1: sodium chlorite; potassium dihydrogenphosphate / 2-methyl-but-2-ene; water; tert-butyl alcohol / 15 h / 20 °C

2: dichloromethane / 15 h / 0 - 20 °C

3: titanium(IV) isopropylate / tetrahydrofuran / 3 h / 0 °C

With titanium(IV) isopropylate; sodium chlorite; potassium dihydrogenphosphate; In tetrahydrofuran; 2-methyl-but-2-ene; dichloromethane; water; tert-butyl alcohol; 3: Kulinkovich cyclopropanation;
DOI:10.1016/j.bmcl.2010.11.115