trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane

Base Information

• Chemical Name: trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane
• CAS No.: 443915-85-3
• Molecular Formula: C₃₉H₄₄O₅Si
• Molecular Weight: 620.861

Synonyms:trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane

Chemical Property of trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane

Chemical Property:

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Technology Process of trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane

There total 6 articles about trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane 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%

(trimethylsilylethynyl)tributyltin (81353-38-0) + 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl acetate (3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,83462-68-4,83462-69-5,94943-10-9,80300-97-6) → trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane (443915-85-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jo020054m

Reference yield:

methyl 2,3,4,6-tetra-O-benzyl α-D-galactopyranoside (3879-79-6) + (trimethylsilylethynyl)tributyltin (81353-38-0) → trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane (443915-85-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol1009976

Reference yield:

1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-68-4,83462-69-5,94943-10-9) + (trimethylsilylethynyl)tributyltin (81353-38-0) → trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane (443915-85-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 5 ℃; for 16.5h;

DOI:10.1039/b414905j

upstream raw materials:

(trimethylsilylethynyl)tributyltin

2,3,4,6-tetra-O-benzyl-D-galactopyranosyl acetate

1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside

2,3,4,6-tetra-O-benzyl-D-galactopyranose

Downstream raw materials:

3-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1H-indole

2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-galactopyranosylethene

1-(2-methoxyethyl)-4-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]triazole

[(2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-ethynyl-tetrahydropyran-2-yl]methyl acetate

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