(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

Base Information

• Chemical Name: (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
• CAS No.: 143921-42-0
• Molecular Formula: C₃₄H₃₆O₉
• Molecular Weight: 588.654

Synonyms:(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

Chemical Property of (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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Technology Process of (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

There total 6 articles about (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 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: 87.0%

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) → (3aS,4R,6S,7R,7aR)-2,2-Dimethyl-6-[(1R,2S,4S,5R,6R)-(3,8,9-trioxa-tricyclo[4.2.1.02,4]non-5-yl)oxy]-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (143921-42-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 25 ℃; for 15h;

DOI:10.1246/cl.1992.1413

Reference yield:

trityl chloride (76-83-5) → (3aS,4R,6S,7R,7aR)-2,2-Dimethyl-6-[(1R,2S,4S,5R,6R)-(3,8,9-trioxa-tricyclo[4.2.1.02,4]non-5-yl)oxy]-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (143921-42-0)

Guidance literature:

Multi-step reaction with 4 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

4: 87 percent / 1 M aq. NaOH / tetrahydrofuran; methanol / 15 h / 25 °C

With pyridine; dmap; sodium hydroxide; (1S)-10-camphorsulfonic acid; sodium methylate; acetic anhydride; In tetrahydrofuran; methanol; 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) → (3aS,4R,6S,7R,7aR)-2,2-Dimethyl-6-[(1R,2S,4S,5R,6R)-(3,8,9-trioxa-tricyclo[4.2.1.02,4]non-5-yl)oxy]-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (143921-42-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 87 percent / 1 M aq. NaOH / tetrahydrofuran; methanol / 15 h / 25 °C

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

DOI:10.1246/cl.1992.1413

upstream raw materials:

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

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

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,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

(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

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