(2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

Base Information

Chemical Name:(2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate
CAS No.:130860-94-5
Molecular Formula:C₃₃H₄₂O₈
Molecular Weight:566.692
Hs Code.:

Synonyms:(2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

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Chemical Property of (2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

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Technology Process of (2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

There total 11 articles about (2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate 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: 88.0%

: 139631-48-4
(2E)-ethyl 2,3,10,11-tetradeoxy-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

: 67-64-1
acetone

: 130860-94-5
(2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

Guidance literature:: With sulfuric acid; for 18h; Ambient temperature;

Reference yield:

: 130860-91-2
*,R^*)>-diethyl (2E,6E)-4,5-bis(phenylmethoxy)-2,6-octadienedioate

: 130860-94-5
(2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

Guidance literature:: Multi-step reaction with 10 steps

1: 71 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 18 h / Ambient temperature

2: 100 percent / 2,6-dimethyllutidine / CH₂Cl₂ / 14 h / Ambient temperature

3: 82 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4: 1.) oxalyl chloride, DMSO / 1.) dichloromethane, -78 deg C, 15 min, 2.) dichloromethane, -78 deg C, 20 min

5: 82 percent / pyridine / toluene; tetrahydrofuran / 5 h / -78 - -10 °C

6: 95 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / -78 °C

7: 1.) oxalyl chloride, DMSO / 1.) dichlromethane, -78 deg C, 20 min, 2.) dichloromethane, -78 deg C, 1 h

8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, RT, 5 h

9: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C

10: 88 percent / concd. H₂SO₄ / 18 h / Ambient temperature

With pyridine; 2,6-dimethyllutidine; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; acetone; toluene;

Reference yield:

: 130860-92-3
diethyl 2,3,6,7-tetrakis-O-<(1,1-dimethylethyl)dimethylsilyl>-4,5-bis-O-(phenylmethyl)-D-threo-L-galacto-octarate

: 130860-94-5
(2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

Guidance literature:: Multi-step reaction with 8 steps

1: 82 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

2: 1.) oxalyl chloride, DMSO / 1.) dichloromethane, -78 deg C, 15 min, 2.) dichloromethane, -78 deg C, 20 min

3: 82 percent / pyridine / toluene; tetrahydrofuran / 5 h / -78 - -10 °C

4: 95 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / -78 °C

5: 1.) oxalyl chloride, DMSO / 1.) dichlromethane, -78 deg C, 20 min, 2.) dichloromethane, -78 deg C, 1 h

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, RT, 5 h

7: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C

8: 88 percent / concd. H₂SO₄ / 18 h / Ambient temperature

With pyridine; n-butyllithium; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene;