(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS No.: 144368-78-5
• Molecular Formula: C₅₈H₆₂O₁₁
• Molecular Weight: 935.124

Synonyms:

Chemical Property of (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole

There total 3 articles about (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole 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: 65.0%

ethyl 2,3,4-tri-O-benzyl-1-thio-6-O-(triphenylmethyl)-β-D-glucopyranoside (144368-77-4) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole (144368-78-5,144368-79-6)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; In 1,2-dichloro-ethane; for 10h;

DOI:10.1016/0008-6215(92)80066-A

Reference yield:

pent-4-enyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside (144368-75-2) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole (144368-78-5,144368-79-6) + (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole (144368-78-5,144368-79-6)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; In 1,2-dichloro-ethane; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0008-6215(92)80066-A

Reference yield:

pent-4-enyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside (144368-75-2) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole (144368-78-5,144368-79-6) + (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxole (144368-78-5,144368-79-6)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; In 1,2-dichloro-ethane; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0008-6215(92)80066-A

upstream raw materials:

ethyl 2,3,4-tri-O-benzyl-1-thio-6-O-(triphenylmethyl)-β-D-glucopyranoside

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

pent-4-enyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside

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