(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

Base Information

• Chemical Name: (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
• CAS No.: 143921-52-2
• Molecular Formula: C₆₁H₆₄O₁₃
• Molecular Weight: 1005.17

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 55.0%

perbenzyl fucosyl bromide (33639-77-9) + (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) → (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[4.2.1.02,4]nonane (143921-52-2)

Guidance literature:

With tetraethylammonium bromide; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 25 ℃; for 20h;

DOI:10.1246/cl.1992.1413

Reference yield:

trityl chloride (76-83-5) → (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[4.2.1.02,4]nonane (143921-52-2)

Guidance literature:

Multi-step reaction with 5 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

5: 55 percent / Et₄NBr, 4 A MS / 1,2-dichloro-ethane; dimethylformamide / 20 h / 25 °C

With pyridine; dmap; sodium hydroxide; (1S)-10-camphorsulfonic acid; tetraethylammonium bromide; sodium methylate; acetic anhydride; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; 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) → (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[4.2.1.02,4]nonane (143921-52-2)

Guidance literature:

Multi-step reaction with 4 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

4: 55 percent / Et₄NBr, 4 A MS / 1,2-dichloro-ethane; dimethylformamide / 20 h / 25 °C

With pyridine; dmap; sodium hydroxide; (1S)-10-camphorsulfonic acid; tetraethylammonium bromide; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1246/cl.1992.1413

upstream raw materials:

perbenzyl fucosyl bromide

(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

trityl chloride

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

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