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

Base Information

Chemical Name:(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid ethyl ester
CAS No.:135663-60-4
Molecular Formula:C₂₀H₃₀O₃S₂
Molecular Weight:382.588
Hs Code.:

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

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

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

There total 8 articles about (2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic 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: 83.0%

: 135663-58-0
(E)-(2R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hex-3-enoic acid ethyl ester

: 135663-60-4
(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid ethyl ester

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

: 135663-60-4
(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 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

8: 83 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; RhCl(PPh₃)3; 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

: 135663-60-4
(2R,5S)-5-Benzyloxy-6-[1,3]dithian-2-yl-2-methyl-hexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 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

7: 83 percent / H₂ / RhCl(PPh₃)3 / benzene / 72 h / 23 °C / 760 Torr

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