(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid methyl ester

Base Information

Chemical Name:(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid methyl ester
CAS No.:135663-61-5
Molecular Formula:C₁₉H₂₈O₃S₂
Molecular Weight:368.562
Hs Code.:

Synonyms:(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid methyl ester

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Chemical Property of (2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid methyl ester

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Technology Process of (2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid methyl ester

There total 18 articles about (2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic 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: 95.0%

: 135663-59-1
(E)-(2R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hex-3-enoic acid methyl ester

: 135663-61-5
(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid methyl ester

Guidance literature:: With hydrogen; RhCl(PPh₃)3; In benzene; at 23 ℃; for 72h; under 760 Torr;
DOI:10.1021/jo00020a027

Reference yield:

: 100-39-0
benzyl bromide

: 135663-61-5
(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

6: 1) CuCN, LiBr, BF₃*OEt₂ / 1) THF, Et₂O, -78 deg C, 5 min, 2) THF, -78 deg C, 30 min

7: 95 percent / H₂ / RhCl(PPh₃)3 / benzene / 72 h / 23 °C / 760 Torr

With pyridine; lead(IV) acetate; 18-crown-6 ether; boron trifluoride diethyl etherate; tetrabutylammomium bromide; hydrogen; potassium hexamethylsilazane; bis(tri-n-butyltin)oxide; lithium bromide; dmap; RhCl(PPh₃)3; In dichloromethane; benzene;
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

: 135663-61-5
(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 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

7: 1) CuCN, LiBr, BF₃*OEt₂ / 1) THF, Et₂O, -78 deg C, 5 min, 2) THF, -78 deg C, 30 min

8: 1) CuCN, LiBr, BF₃*OEt₂ / 1) THF, Et₂O, -78 deg C, 5 min, 2) THF, -78 deg C, 30 min

9: 95 percent / H₂ / RhCl(PPh₃)3 / benzene / 72 h / 23 °C / 760 Torr

With pyridine; lead(IV) acetate; potassium fluoride; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; lithium bromide; RhCl(PPh₃)3; In dichloromethane; acetonitrile; benzene;
DOI:10.1021/jo00020a027