((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester

Base Information

Chemical Name:((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester
CAS No.:269715-94-8
Molecular Formula:C₁₉H₂₇N₃O₄
Molecular Weight:361.441
Hs Code.:

Synonyms:((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester

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Chemical Property of ((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester

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Technology Process of ((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester

There total 14 articles about ((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl 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: 84.0%

: 269715-93-7
[6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl]-carbamic acid benzyl ester

: 269715-94-8
((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(99)02348-5

Reference yield:

: 269715-77-7
3-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid tert-butyl ester

: 269715-94-8
((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 89 percent / DIBAL-H / toluene / -78 °C

2: 51 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

3: 100 percent / 2,6-lutidine

4: 90 percent / Et₃N

5: 91 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

6: 64 percent / LDA / tetrahydrofuran

7: 74 percent / pTSA / benzene / Heating

8: 100 percent / H₂ / Pd/C

9: 85 percent / HgCl₂; Et₃N / dimethylformamide

10: 100 percent / NaBH₄ / methanol

11: 63 percent / PPh₃; DIAD

12: 67 percent / NaH / tetrahydrofuran; methanol

13: 84 percent / TBAF / tetrahydrofuran

With 2,6-dimethylpyridine; sodium tetrahydroborate; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; triethylamine; triphenylphosphine; mercury dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1: Reduction / 2: allylation / 3: Etherification / 4: Acylation / 5: ozonolysis / 6: Wittig reaction / 7: Cyclization / 8: Hydrogenolysis / 9: Substitution / 10: Reduction / 11: Cyclization / 12: Substitution / 13: Substitution;
DOI:10.1016/S0040-4039(99)02348-5

Reference yield:

: 269715-79-9
[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-3-oxo-propyl]-carbamic acid benzyl ester

: 269715-94-8
((3R,4aS,6S,7R,8S)-6-Hydroxy-8-hydroxymethyl-3,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-yl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 51 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

2: 100 percent / 2,6-lutidine

3: 90 percent / Et₃N

4: 91 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

5: 64 percent / LDA / tetrahydrofuran

6: 74 percent / pTSA / benzene / Heating

7: 100 percent / H₂ / Pd/C

8: 85 percent / HgCl₂; Et₃N / dimethylformamide

9: 100 percent / NaBH₄ / methanol

10: 63 percent / PPh₃; DIAD

11: 67 percent / NaH / tetrahydrofuran; methanol

12: 84 percent / TBAF / tetrahydrofuran

With 2,6-dimethylpyridine; sodium tetrahydroborate; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; triphenylphosphine; mercury dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: allylation / 2: Etherification / 3: Acylation / 4: ozonolysis / 5: Wittig reaction / 6: Cyclization / 7: Hydrogenolysis / 8: Substitution / 9: Reduction / 10: Cyclization / 11: Substitution / 12: Substitution;
DOI:10.1016/S0040-4039(99)02348-5