(2-Chloro-acetyl)-carbamic acid (5S,8R,9R,10R)-10-hydroxy-9-methoxy-2-oxo-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

Base Information

Chemical Name:(2-Chloro-acetyl)-carbamic acid (5S,8R,9R,10R)-10-hydroxy-9-methoxy-2-oxo-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]dec-8-yl ester
CAS No.:176719-67-8
Molecular Formula:C₂₂H₂₈ClNO₉
Molecular Weight:485.919
Hs Code.:

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Chemical Property of (2-Chloro-acetyl)-carbamic acid (5S,8R,9R,10R)-10-hydroxy-9-methoxy-2-oxo-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

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Technology Process of (2-Chloro-acetyl)-carbamic acid (5S,8R,9R,10R)-10-hydroxy-9-methoxy-2-oxo-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

There total 9 articles about (2-Chloro-acetyl)-carbamic acid (5S,8R,9R,10R)-10-hydroxy-9-methoxy-2-oxo-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]dec-8-yl 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: 50.0%

: 4461-30-7
2-chloroacetylisocyanate

: (5S,8R,9R,10R)-8,10-Dihydroxy-9-methoxy-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]decan-2-one

: 176719-67-8
(2-Chloro-acetyl)-carbamic acid (5S,8R,9R,10R)-10-hydroxy-9-methoxy-2-oxo-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

Guidance literature:: In dichloromethane; at 0 ℃;
DOI:10.1016/S0960-894X(96)00564-1

Reference yield:

: 69351-19-5,18422-53-2
Shi's ketone

: 176719-67-8
(2-Chloro-acetyl)-carbamic acid (5S,8R,9R,10R)-10-hydroxy-9-methoxy-2-oxo-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: n-BuLi / tetrahydrofuran / -78 °C

2: 85 percent / H₂ / Lindlar catalyst / benzene / Ambient temperature

3: 90 percent / acetic acid; H₂O / Ambient temperature

4: 1.) Bu₂SnO / 1.) MeOH, reflux, 2.) dioxane, reflux

5: 92 percent / NaH, NBu₄I / tetrahydrofuran / Ambient temperature

6: 74 percent / acidic resin / tetrahydrofuran; H₂O / 70 °C

7: 68 percent / tetrahydrofuran; CH₂Cl₂ / Heating

8: 92 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

9: 50 percent / CH₂Cl₂ / 0 °C

With n-butyllithium; acidic resin; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; water; acetic acid; ethyl acetate; benzene;
DOI:10.1016/S0960-894X(96)00564-1

Reference yield:

: 1823-14-9
5-phenyl-1-pentyne

: 176719-67-8
(2-Chloro-acetyl)-carbamic acid (5S,8R,9R,10R)-10-hydroxy-9-methoxy-2-oxo-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: n-BuLi / tetrahydrofuran / -78 °C

2: 85 percent / H₂ / Lindlar catalyst / benzene / Ambient temperature

3: 90 percent / acetic acid; H₂O / Ambient temperature

4: 1.) Bu₂SnO / 1.) MeOH, reflux, 2.) dioxane, reflux

5: 92 percent / NaH, NBu₄I / tetrahydrofuran / Ambient temperature

6: 74 percent / acidic resin / tetrahydrofuran; H₂O / 70 °C

7: 68 percent / tetrahydrofuran; CH₂Cl₂ / Heating

8: 92 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

9: 50 percent / CH₂Cl₂ / 0 °C

With n-butyllithium; acidic resin; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; water; acetic acid; ethyl acetate; benzene;
DOI:10.1016/S0960-894X(96)00564-1