Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl ester

Base Information

Chemical Name:Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl ester
CAS No.:176439-77-3
Molecular Formula:C₆₆H₆₈N₂O₁₅S
Molecular Weight:1161.34
Hs Code.:

Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl ester

Synonyms:Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl ester

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Chemical Property of Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl ester

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Technology Process of Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl ester

There total 9 articles about Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl 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: 100.0%

: 108-24-7
acetic anhydride

: 176439-76-2
Toluene-4-sulfonic acid (2S,3R,4R,5R)-4-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,6-bis-benzyloxy-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-hexyl ester

: 176439-77-3
Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl ester

Guidance literature:: With pyridine; Ambient temperature;
DOI:10.1016/0040-4020(96)00791-0

Reference yield:

: 85-44-9
phthalic anhydride

: 176439-77-3
Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl ester

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 80 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

4: 100 percent / pyridine / Ambient temperature

With pyridine; dmap; sodium methylate; triethylamine; In methanol; dichloromethane;
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

: 176439-77-3
Acetic acid (1R,2S,3R,4S)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-1-benzyloxymethyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(toluene-4-sulfonyloxy)-pentyl ester

Guidance literature:: Multi-step reaction with 8 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

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