Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside

Base Information

Chemical Name:Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside
CAS No.:139655-28-0
Molecular Formula:C₃₆H₄₇NO₅Si
Molecular Weight:601.858
Hs Code.:

Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside

Synonyms:Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside

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Chemical Property of Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside

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Technology Process of Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside

There total 12 articles about Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside 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%

: 67-56-1
methanol

: 139631-17-7,139631-18-8
(2S,4S,5S,7E,9E,11E)-4-((tert-Butyldiphenylsilyl)oxy)-1,2-(isopropylidenedioxy)-5,7,11-trimethyl-12-(2'-methyloxazol-4'-yl)-7,9,11-dodecatrien-6-one

: 139655-28-0
Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside

Guidance literature:: With pyridinium p-toluenesulfonate; In diethyl ether; at 50 ℃;
DOI:10.1021/jo00034a010

Reference yield:

: 10200-43-8
2-methyl-4-carbethoxy-1,3-oxazole

: 139655-28-0
Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 56 percent / diisobutylaluminum hydride / diethyl ether; hexane / 0.21 h / -78 °C

2: 85 percent / benzene / 22 h / 80 °C

3: 1.) NaH / 1.) toluene, oil, 40 deg C, 1.5 h, 2.) 110 deg C, 24 h

4: 89 percent / diisobutylaluminum hydride / diethyl ether; hexane / 1.5 h / -78 °C

5: 88 percent / MnO₂ / CH₂Cl₂ / 20 h / 0 to 23 deg C gradually

6: 1.) NaH / 1.) THF, oil, -35 to -10 deg C, 30 min, then to 0 deg C, 1 h, then 22 deg C, 30 min, 2.) -35 to 23, 17 h

7: 83 percent / pyridinium p-toluenesulfonate / diethyl ether / 50 °C

With manganese(IV) oxide; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; In diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/jo00034a010

Reference yield:

: 113732-84-6
2-methyl-1,3-oxazole-4-carbaldehyde

: 139655-28-0
Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / benzene / 22 h / 80 °C

2: 1.) NaH / 1.) toluene, oil, 40 deg C, 1.5 h, 2.) 110 deg C, 24 h

3: 89 percent / diisobutylaluminum hydride / diethyl ether; hexane / 1.5 h / -78 °C

4: 88 percent / MnO₂ / CH₂Cl₂ / 20 h / 0 to 23 deg C gradually

5: 1.) NaH / 1.) THF, oil, -35 to -10 deg C, 30 min, then to 0 deg C, 1 h, then 22 deg C, 30 min, 2.) -35 to 23, 17 h

6: 83 percent / pyridinium p-toluenesulfonate / diethyl ether / 50 °C

With manganese(IV) oxide; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; In diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/jo00034a010