2,4,6-Triisopropyl-benzenesulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-((3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Base Information

• Chemical Name: 2,4,6-Triisopropyl-benzenesulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-((3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester
• CAS No.: 143921-47-5
• Molecular Formula: C₄₉H₆₀O₁₂S
• Molecular Weight: 873.074

Synonyms:2,4,6-Triisopropyl-benzenesulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-((3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Chemical Property of 2,4,6-Triisopropyl-benzenesulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-((3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

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Technology Process of 2,4,6-Triisopropyl-benzenesulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-((3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

There total 4 articles about 2,4,6-Triisopropyl-benzenesulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-((3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl 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:

trityl chloride (76-83-5) → 2,4,6-Triisopropyl-benzenesulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-((3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester (143921-47-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) pyridine, 2.) Ac₂O, pyridine, 3.) NaOMe

2: 10-camphorsulfonic acid / dimethylformamide / 6 h / 60 °C / 20 Torr

3: dimethylaminopyridine (DMAP), pyridine / 18 h / 25 °C

With pyridine; dmap; (1S)-10-camphorsulfonic acid; sodium methylate; acetic anhydride; In N,N-dimethyl-formamide;

DOI:10.1246/cl.1992.1413

Reference yield:

4-O-(6-O-triphenylmethyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-β-D-glucopyranose (73139-43-2) → 2,4,6-Triisopropyl-benzenesulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-((3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester (143921-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 10-camphorsulfonic acid / dimethylformamide / 6 h / 60 °C / 20 Torr

2: dimethylaminopyridine (DMAP), pyridine / 18 h / 25 °C

With pyridine; dmap; (1S)-10-camphorsulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1246/cl.1992.1413

Reference yield:

Acetic acid (3aS,4R,6S,7R,7aS)-6-((1R,2R,3S,4R,5R)-3,4-diacetoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester (143921-45-3) → 2,4,6-Triisopropyl-benzenesulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-((3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester (143921-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol

2: dimethylaminopyridine (DMAP), pyridine / 18 h / 25 °C

With pyridine; dmap; sodium methylate; In methanol;

DOI:10.1246/cl.1992.1413

upstream raw materials:

trityl chloride

4-O-(6-O-triphenylmethyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-β-D-glucopyranose

Acetic acid (3aS,4R,6S,7R,7aS)-6-((1R,2R,3S,4R,5R)-3,4-diacetoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

O-β-D-galactopyranosyl-(1<*>4)-1,6-anhydro-β-D-glucopyranoside

Downstream raw materials:

(1R,2S,4S,5R,6R)-5-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonane

(1R,2S,3R,4R,5R)-4-Azido-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

(1R,2S,4S,5R,6R)-5-[(3aS,4R,6S,7R,7aS)-2,2-Dimethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonane

(3aS,4R,6S,7R,7aR)-2,2-Dimethyl-6-[(1R,2S,4S,5R,6R)-(3,8,9-trioxa-tricyclo[4.2.1.0^2,4]non-5-yl)oxy]-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

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