4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

Base Information

Chemical Name:4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester
CAS No.:352522-32-8
Molecular Formula:C₆₂H₁₀₉NO₁₁
Molecular Weight:1044.55
Hs Code.:

4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

Synonyms:4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

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Chemical Property of 4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

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Technology Process of 4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

There total 8 articles about 4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl 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: 95.0%

: 352522-29-3
4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-7,9-O-isopropylidene-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

: 352522-32-8
4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 2h;
DOI:10.1016/S0008-6215(01)00290-7

Reference yield:

: 1663-39-4,25232-27-3
tert-Butyl acrylate

: 352522-32-8
4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 60 percent / 2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile); Bu₃SnH / diethyl ether / 1 h / 20 °C

2: H₂ / Pd(OH)2/C / ethanol / 0.33 h / 20 °C

3: 626 mg / 3-(3-dimrthylaminopropyl)-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 °C

4: NaOMe / methanol / 0.33 h / 20 °C

5: 485 mg / TsOH*H₂O / dimethylformamide / 1 h / 20 °C

6: 88 percent / DMAP; DCC / CH₂Cl₂ / 7 h / 20 °C

7: 95 percent / TsOH*H₂O / methanol / 2 h / 20 °C

With dmap; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; hydrogen; tri-n-butyl-tin hydride; sodium methylate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; palladium dihydroxide; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00290-7

Reference yield:

: 73446-41-0
3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide

: 352522-32-8
4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 60 percent / 2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile); Bu₃SnH / diethyl ether / 1 h / 20 °C

2: H₂ / Pd(OH)2/C / ethanol / 0.33 h / 20 °C

3: 626 mg / 3-(3-dimrthylaminopropyl)-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 °C

4: NaOMe / methanol / 0.33 h / 20 °C

5: 485 mg / TsOH*H₂O / dimethylformamide / 1 h / 20 °C

6: 88 percent / DMAP; DCC / CH₂Cl₂ / 7 h / 20 °C

7: 95 percent / TsOH*H₂O / methanol / 2 h / 20 °C

With dmap; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; hydrogen; tri-n-butyl-tin hydride; sodium methylate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; palladium dihydroxide; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00290-7