((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester

Base Information

Chemical Name:((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester
CAS No.:315229-38-0
Molecular Formula:C₁₇H₂₆N₂O₈
Molecular Weight:386.402
Hs Code.:

Synonyms:((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester

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Chemical Property of ((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester

Chemical Property:

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Technology Process of ((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester

There total 1 articles about ((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl 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: 81.0%

: 3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0
2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

: 5680-79-5,883886-67-7
glycine ethyl ester hydrochloride

: 315229-38-0
((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester

Guidance literature:: With sodium cyanoborohydride; In methanol; for 24h; Heating;
DOI:10.1016/S0040-4020(00)00787-0

Reference yield: 96.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 315229-38-0
((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester

: 315229-39-1
[((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester

Guidance literature:: In methanol; at 25 ℃;
DOI:10.1016/S0040-4020(00)00787-0

Reference yield:

: 315229-38-0
((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester

: ethyl {(6S)-6-(hydroxymethyl)-2-oxo-4-[2-(benzyloxycarbonylamino)acetyl]piperazin-1-yl}acetate

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / methanol / 25 °C

2: NaIO₄ / H₂O; CH₂Cl₂ / 1 h / 0 °C

3: 1.75 g / NaBH₄ / methanol / 1 h / 0 °C

4: 75 percent / H₂ / Pd/C / methanol / 24 h / 25 °C

5: 98 percent / imidazole / dimethylformamide / 5 h / 25 °C

6: 96 percent / NaH; 18-crown-6 / dimethylformamide / 4 h / 25 °C

7: 98 percent / Bu₄NF / tetrahydrofuran / 0 °C

8: 59 percent / HCl(g) / diethyl ether / 0.25 h / 0 °C

9: 43 percent / Et₃N; EDC / CH₂Cl₂ / 13 h / 0 - 25 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Acylation / 2: Oxidation / 3: Reduction / 4: Hydrogenolysis / 5: silylation / 6: Alkylation / 7: desilylation / 8: Hydrolysis / 9: Condensation;
DOI:10.1016/S0040-4020(00)00787-0