N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

Base Information

Chemical Name:N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide
CAS No.:176439-79-5
Molecular Formula:C₅₁H₅₉N₅O₁₀
Molecular Weight:902.057
Hs Code.:

N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

Synonyms:N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

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Chemical Property of N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

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Technology Process of N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

There total 12 articles about N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide 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: 29.0%

: 176439-80-8
N-{(2S,3R,4R,5S,6R)-2-[(1S,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-(2-benzyloxy-acetyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

: 176439-79-5
N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

: 176588-82-2
N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -60 ℃; for 4.5h;
DOI:10.1016/0040-4020(96)00791-0

Reference yield:

: 147314-92-9
allyl O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

: 176439-79-5
N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 11 steps

1: 98 percent / t-BuOK / dimethylformamide / 3 h / 75 °C

2: 2M HCl / CHCl₃; methanol / 20 h / Ambient temperature

3: 72 percent / NaBH₄ / ethanol; tetrahydrofuran / 18 h / -20 - 20 °C

4: 100 percent / 1M NaOH / 2-methoxy-ethanol / 8 h / 90 °C

5: 1.) Et₃N, 2.) pyridine / 1.) CH₃OH, RT, 2.) MeOH, 80 deg C, 7 h

6: 95 percent / NaOMe / methanol / 2 h / Ambient temperature

7: 80 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

8: 100 percent / pyridine / Ambient temperature

9: 71 percent / NaN₃ / dimethylformamide / 8 h / 100 °C

10: aq. CH₃NH₂ / ethanol / 42 h / Ambient temperature

11: methanol / 0.17 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; sodium azide; potassium tert-butylate; sodium methylate; triethylamine; methylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; 2-methoxy-ethanol; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(96)00791-0

Reference yield:

: 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-D-glucopyranoside

: 176439-79-5
N-{(2S,3R,4R,5S,6R)-2-[(1R,2R,3S)-3-Acetylamino-4-azido-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-butoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 9 steps

1: 72 percent / NaBH₄ / ethanol; tetrahydrofuran / 18 h / -20 - 20 °C

2: 100 percent / 1M NaOH / 2-methoxy-ethanol / 8 h / 90 °C

3: 1.) Et₃N, 2.) pyridine / 1.) CH₃OH, RT, 2.) MeOH, 80 deg C, 7 h

4: 95 percent / NaOMe / methanol / 2 h / Ambient temperature

5: 80 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

6: 100 percent / pyridine / Ambient temperature

7: 71 percent / NaN₃ / dimethylformamide / 8 h / 100 °C

8: aq. CH₃NH₂ / ethanol / 42 h / Ambient temperature

9: methanol / 0.17 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; sodium azide; sodium methylate; triethylamine; methylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; 2-methoxy-ethanol; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(96)00791-0