(3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester
CAS No.:269715-91-5
Molecular Formula:C₃₉H₆₁N₃O₆Si₂
Molecular Weight:724.101
Hs Code.:

(3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

Synonyms:(3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

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Chemical Property of (3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

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Technology Process of (3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

There total 13 articles about (3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic 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: 63.0%

: 269715-90-4
{[(E)-Benzyloxycarbonylimino]-[(2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-hydroxy-propyl)-3-methyl-piperidin-1-yl]-methyl}-carbamic acid benzyl ester

: 269715-91-5
(3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

: (3S,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine;
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

: 269715-91-5
(3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 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

With 2,6-dimethylpyridine; sodium tetrahydroborate; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; hydrogen; 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;
DOI:10.1016/S0040-4039(99)02348-5

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 269715-91-5
(3R,4aS,6S,7R,8S)-1-[(E)-Benzyloxycarbonylimino]-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-hexahydro-pyrido[1,2-c]pyrimidine-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / 2,6-lutidine

2: 90 percent / Et₃N

3: 91 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

4: 64 percent / LDA / tetrahydrofuran

5: 74 percent / pTSA / benzene / Heating

6: 100 percent / H₂ / Pd/C

7: 85 percent / HgCl₂; Et₃N / dimethylformamide

8: 100 percent / NaBH₄ / methanol

9: 63 percent / PPh₃; DIAD

With 2,6-dimethylpyridine; sodium tetrahydroborate; di-isopropyl azodicarboxylate; hydrogen; 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: Etherification / 2: Acylation / 3: ozonolysis / 4: Wittig reaction / 5: Cyclization / 6: Hydrogenolysis / 7: Substitution / 8: Reduction / 9: Cyclization;
DOI:10.1016/S0040-4039(99)02348-5