6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-D-glycero-D-ido-nononic acid tert-butyl ester

Base Information

Chemical Name:6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-D-glycero-D-ido-nononic acid tert-butyl ester
CAS No.:352522-20-4
Molecular Formula:C₂₇H₃₇NO₁₁
Molecular Weight:551.591
Hs Code.:

Synonyms:6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-D-glycero-D-ido-nononic acid tert-butyl ester

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Chemical Property of 6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-D-glycero-D-ido-nononic acid tert-butyl ester

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Technology Process of 6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-D-glycero-D-ido-nononic acid tert-butyl ester

There total 1 articles about 6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-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: 60.0%

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

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

: 352522-20-4
6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-D-glycero-D-ido-nononic acid tert-butyl ester

Guidance literature:: With 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; tri-n-butyl-tin hydride; In diethyl ether; at 20 ℃; for 1h;
DOI:10.1016/S0008-6215(01)00290-7

Reference yield:

: 352522-20-4
6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-D-glycero-D-ido-nononic acid tert-butyl ester

: 352522-44-2
4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-7-O-diphenylphosphono-9-O-methyl-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

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

2: 626 mg / 3-(3-dimrthylaminopropyl)-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 °C

3: NaOMe / methanol / 0.33 h / 20 °C

4: 485 mg / TsOH*H₂O / dimethylformamide / 1 h / 20 °C

5: 88 percent / DMAP; DCC / CH₂Cl₂ / 7 h / 20 °C

6: 95 percent / TsOH*H₂O / methanol / 2 h / 20 °C

7: 93 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

8: 94 percent / DMAP / CH₂Cl₂ / 4 h / 20 °C

9: 99 percent / H₂ / Pd(en)/C / tetrahydrofuran / 3 h / 20 °C

10: 85 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 20 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; hydrogen; sodium methylate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; palladium dihydroxide; Pd(en)/C; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00290-7

Reference yield:

: 352522-20-4
6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-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:: Multi-step reaction with 6 steps

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

2: 626 mg / 3-(3-dimrthylaminopropyl)-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 °C

3: NaOMe / methanol / 0.33 h / 20 °C

4: 485 mg / TsOH*H₂O / dimethylformamide / 1 h / 20 °C

5: 88 percent / DMAP; DCC / CH₂Cl₂ / 7 h / 20 °C

6: 95 percent / TsOH*H₂O / methanol / 2 h / 20 °C

With dmap; hydrogen; sodium methylate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; palladium dihydroxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00290-7