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

Base Information

• Chemical Name: trimethyl-[2-[(2R,3S,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane
• CAS No.: 141100-79-0
• Molecular Formula: C₃₉H₄₄O₅Si
• Molecular Weight: 620.861
• Mol file: 141100-79-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about trimethyl-[2-[(2R,3S,4R,5R,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: 65.0%

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose (80300-30-7) + (trimethylsilylethynyl)tributyltin (81353-38-0) → trimethyl-[2-[(2R,3S,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane (141100-79-0)

Guidance literature:

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

DOI:10.1021/jo020054m

Reference yield: 64.0%

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride (78153-79-4,89025-46-7,94898-42-7,94898-43-8,101966-50-1,143615-35-4,122741-44-0) + potassium trifluoro(2-trimethylsilylethynyl)boranuide → trimethyl-[2-[(2R,3S,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane (141100-79-0)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at -40 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ol102473k

Reference yield: 25.0%

(trimethylsilylethynyl)tributyltin (81353-38-0) + 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside (56822-49-2) → trimethyl-[2-[(2R,3S,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane (141100-79-0)

Guidance literature:

(trimethylsilylethynyl)tributyltin; 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1.5h; Molecular sieve;

With triethylamine; In dichloromethane;

upstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide

diethyl[(trimethylsilyl)acetylenyl]aluminum

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

trimethylsilylacetylene

Downstream raw materials:

4,5,6,8-tetra-O-acetyl-3,7-anhydro-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethysilyl)-D-glycero-D-gulo-octitol

(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran

C₂₃H₂₇N₃O₉

C₂₄H₂₉N₃O₉