(-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone

Base Information

Chemical Name:(-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone
CAS No.:176540-24-2
Molecular Formula:C₂₃H₂₇ClO₉Se
Molecular Weight:561.875
Hs Code.:

(-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone

Synonyms:(-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone

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Chemical Property of (-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone

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Technology Process of (-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone

There total 5 articles about (-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone 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: 90.0%

: (+)-(1R,4S,5S,6S)-5-benzeneselenyl-6-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one

: 176540-21-9
(-)-(1S,5R,6R,7S)-6,7-bis(methoxymethoxy)-2,8-dioxabicyclo<3.2.1>octan-3-one

: 176540-24-2
(-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone

Guidance literature:: (-)-(1S,5R,6R,7S)-6,7-bis(methoxymethoxy)-2,8-dioxabicyclo<3.2.1>octan-3-one; With n-butyllithium; (Me₂Si)2NLi; In tetrahydrofuran; hexane; at -78 ℃; for 0.666667h;

(+)-(1R,4S,5S,6S)-5-benzeneselenyl-6-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1055/s-1999-3645

Reference yield: 90.0%

: Lithium; (1R,4S,5S,6S)-3-((1S,4S,5R,6R,7S)-6,7-bis-methoxymethoxy-3-oxo-2,8-dioxa-bicyclo[3.2.1]oct-4-ylmethyl)-6-chloro-5-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-en-2-olate

: 176540-24-2
(-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone

Guidance literature:: With methanol; acetic acid; at -78 ℃;
DOI:10.1016/0040-4039(96)00189-X

Reference yield:

: (+)-(1R,4S,5S,6S)-5-benzeneselenyl-6-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one

: (+/-)-6-exo,7-endo-Bis(methoxymethoxy)-2,8-dioxabicyclo[3.2.1]octan-3-one

: 176540-24-2
(-)-5-Deoxy-5-{(1''S,2''S,4''R,5''S,6''S)-[5''-endo-chloro-6''-exo-phenylseleno-3''-oxo-7''-oxabicyclo[2.2.1]hept-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone

: (1R,4R,5S,6S,7R)-4-((1S,2R,3S,4R,5S,6S)-5-Chloro-3-hydroxy-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl)-6,7-bis-methoxymethoxy-2,8-dioxa-bicyclo[3.2.1]octan-3-one

Guidance literature:: (+/-)-6-exo,7-endo-Bis(methoxymethoxy)-2,8-dioxabicyclo[3.2.1]octan-3-one; With n-butyllithium; (Me₂Si)2NLi; In tetrahydrofuran; hexane; at -78 ℃; for 0.666667h;

(+)-(1R,4S,5S,6S)-5-benzeneselenyl-6-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 0.25h; Title compound not separated from byproducts;
DOI:10.1055/s-1999-3645