5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal

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Chemical Name:5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal
CAS No.:466680-62-6
Molecular Formula:C₃₆H₄₈O₁₄
Molecular Weight:704.769
Hs Code.:

Synonyms:5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal

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Chemical Property of 5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal

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Technology Process of 5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal

There total 5 articles about 5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal 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%

: 466680-61-5
Acetic acid (1S,2S)-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-formyl-ethyl ester

: 466680-62-6
5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal

Guidance literature:: Acetic acid (1S,2S)-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-formyl-ethyl ester; With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydrogencarbonate; potassium bromide; at 0 ℃; for 0.75h;

With sodium hypochlorite; sodium hydrogencarbonate; sodium chloride; at 20 ℃;
DOI:10.1016/S0008-6215(02)00084-8

Reference yield:

: 264919-23-5
4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

: 466680-62-6
5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylammonium chloride / CH₂Cl₂ / 1.25 h / 20 °C

2.1: pyridine / 15 h / 20 °C

3.1: pyridinium tosylate / methanol / 0.5 h / 20 °C

4.1: 4 Angstroem MS; NMO; TPAP / 2 h / 20 °C

5.1: TEMPO; satd aq NaHCO₃/KBr; B₄NCl / 0.75 h / 0 °C

5.2: 80 percent / NaClO; satd aq NaCl; satd aq NaHCO₃ / 20 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; pyridinium p-toluenesulfonate; triethylamine hydrochloride; sodium hydrogencarbonate; potassium bromide; In methanol; dichloromethane;
DOI:10.1016/S0008-6215(02)00084-8

Reference yield:

: Acetic acid (1R,2R)-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-(2-methoxy-propoxymethyl)-ethyl ester

: 466680-62-6
5-O-acetyl-4-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronic acid dimethyl acetal

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridinium tosylate / methanol / 0.5 h / 20 °C

2.1: 4 Angstroem MS; NMO; TPAP / 2 h / 20 °C

3.1: TEMPO; satd aq NaHCO₃/KBr; B₄NCl / 0.75 h / 0 °C

3.2: 80 percent / NaClO; satd aq NaCl; satd aq NaHCO₃ / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium bromide; In methanol;
DOI:10.1016/S0008-6215(02)00084-8