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

Base Information

• Chemical Name: Acetic acid (2R,3R)-3-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-propyl ester
• CAS No.: 466680-60-4
• Molecular Formula: C₃₆H₅₀O₁₃
• Molecular Weight: 690.785

Synonyms:

Chemical Property of Acetic acid (2R,3R)-3-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-propyl ester

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Technology Process of Acetic acid (2R,3R)-3-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-propyl ester

There total 3 articles about Acetic acid (2R,3R)-3-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-propyl 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:

Acetic acid (2R,3R)-3-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2-methoxy-propoxy)-propyl ester → Acetic acid (2R,3R)-3-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-propyl ester (466680-60-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 20 ℃; for 0.5h;

DOI:10.1016/S0008-6215(02)00084-8

Reference yield:

4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (264919-23-5) → Acetic acid (2R,3R)-3-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-propyl ester (466680-60-4)

Guidance literature:

Multi-step reaction with 3 steps

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

2: pyridine / 15 h / 20 °C

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

With pyridine; pyridinium p-toluenesulfonate; triethylamine hydrochloride; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(02)00084-8

Reference yield:

(2R,3R)-3-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2-methoxy-propoxy)-propan-1-ol → Acetic acid (2R,3R)-3-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-propyl ester (466680-60-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 15 h / 20 °C

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

With pyridine; pyridinium p-toluenesulfonate; In methanol;

DOI:10.1016/S0008-6215(02)00084-8

upstream raw materials:

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

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