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

Base Information

Chemical Name: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
CAS No.:176439-76-2
Molecular Formula:C₆₄H₆₆N₂O₁₄S
Molecular Weight:1119.3
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 80.0%

: 98-59-9
p-toluenesulfonyl chloride

: 176439-75-1
N-{(2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-2-[(1R,2R,3S)-2-benzyloxy-1-((R)-2-benzyloxy-1-hydroxy-ethyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-butoxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl}-acetamide

: 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

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 4h; Ambient temperature;
DOI:10.1016/0040-4020(96)00791-0

Reference yield:

: 85-44-9
phthalic 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

Guidance literature:: Multi-step reaction with 3 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

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

: 176439-76-2
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

Guidance literature:: Multi-step reaction with 7 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

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