(E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl ester
CAS No.:135663-48-8
Molecular Formula:C₂₀H₂₈O₆S₃
Molecular Weight:460.637
Hs Code.:

Synonyms:(E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl ester

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Chemical Property of (E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl ester

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Technology Process of (E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl ester

There total 6 articles about (E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl 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: 62.0%

: 135663-47-7
Methanesulfonic acid (1S,2R)-2-benzyloxy-3-[1,3]dithian-2-yl-1-formyl-propyl ester

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 135663-48-8
(E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl ester

Guidance literature:: In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1021/jo00020a027

Reference yield:

: 126461-69-6
1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose

: 135663-48-8
(E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / pyridine / 12 h / 23 °C

2: 88 percent / N-iodosuccinimide / acetonitrile / 12 h / 23 °C

3: 1) tributyltin hydride, AIBN, 2) satd.aq.KF / 1) benzene, reflux, 5 h, 2) 12 h

4: 74 percent / BF₃*OEt₂ / CH₂Cl₂ / 24 h / 23 °C

5: 72 percent / lead tetraacetate / benzene / 0.25 h

6: 62 percent / CH₂Cl₂ / 0.25 h / 0 °C

With pyridine; lead(IV) acetate; potassium fluoride; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; In dichloromethane; acetonitrile; benzene;
DOI:10.1021/jo00020a027

Reference yield:

: 135663-44-4
Methanesulfonic acid (2R,3S,4R)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester

: 135663-48-8
(E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / N-iodosuccinimide / acetonitrile / 12 h / 23 °C

2: 1) tributyltin hydride, AIBN, 2) satd.aq.KF / 1) benzene, reflux, 5 h, 2) 12 h

3: 74 percent / BF₃*OEt₂ / CH₂Cl₂ / 24 h / 23 °C

4: 72 percent / lead tetraacetate / benzene / 0.25 h

5: 62 percent / CH₂Cl₂ / 0.25 h / 0 °C

With lead(IV) acetate; potassium fluoride; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; In dichloromethane; acetonitrile; benzene;
DOI:10.1021/jo00020a027