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

Base Information

Chemical Name:(Z)-(4S,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid methyl ester
CAS No.:135695-43-1
Molecular Formula:C₁₉H₂₆O₆S₃
Molecular Weight:446.61
Hs Code.:

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

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

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

There total 16 articles about (Z)-(4S,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid methyl 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:

: 100-39-0
benzyl bromide

: 135695-43-1
(Z)-(4S,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1) (n-Bu₃Sn)2O, 2) Bu₄NBr / 1) toluene, reflux, 4 h, 2) 80 deg C, 5 h

2: 80 percent / pyridine / DMAP / CH₂Cl₂ / 24 h / 23 °C

3: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / 0 - 23 °C

4: 74 percent / Pb(OAc)4 / benzene / 0.5 h / 23 °C

5: 1) KHMDS, 18-crown-6 / 1) toluene, -78 deg C, 2) THF, -78 deg C, 45 min

With pyridine; lead(IV) acetate; 18-crown-6 ether; boron trifluoride diethyl etherate; tetrabutylammomium bromide; potassium hexamethylsilazane; bis(tri-n-butyltin)oxide; dmap; In dichloromethane; benzene;
DOI:10.1021/jo00020a027

Reference yield:

: 135663-52-4,135663-53-5
(2R,3R,4R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol

: 135695-43-1
(Z)-(4S,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / pyridine / DMAP / CH₂Cl₂ / 24 h / 23 °C

2: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / 0 - 23 °C

3: 74 percent / Pb(OAc)4 / benzene / 0.5 h / 23 °C

4: 1) KHMDS, 18-crown-6 / 1) toluene, -78 deg C, 2) THF, -78 deg C, 45 min

With pyridine; lead(IV) acetate; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium hexamethylsilazane; dmap; In dichloromethane; benzene;
DOI:10.1021/jo00020a027

Reference yield:

: 1043893-21-5
Acetic acid (2R,3R,4R)-4-acetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

: 135695-43-1
(Z)-(4S,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1) NaOMe, 2) imidazole / 1) MeOH, 23 deg C, 2 h, 2) DMF, 23 deg C, 16 h

2: 1) (n-Bu₃Sn)2O, 2) Bu₄NBr / 1) toluene, reflux, 4 h, 2) 80 deg C, 5 h

3: 80 percent / pyridine / DMAP / CH₂Cl₂ / 24 h / 23 °C

4: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / 0 - 23 °C

5: 74 percent / Pb(OAc)4 / benzene / 0.5 h / 23 °C

6: 1) KHMDS, 18-crown-6 / 1) toluene, -78 deg C, 2) THF, -78 deg C, 45 min

With pyridine; 1H-imidazole; lead(IV) acetate; 18-crown-6 ether; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium methylate; potassium hexamethylsilazane; bis(tri-n-butyltin)oxide; dmap; In dichloromethane; benzene;
DOI:10.1021/jo00020a027