Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 167646-56-2
• Molecular Formula: C₂₉H₃₄O₅Si
• Molecular Weight: 490.671
• Mol file: 167646-56-2.mol

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester

There total 2 articles about Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester 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: 31.0%

6-O-acetyl-2,3-di-O-benzyl-4-deoxy-4-C-ethynyl-D-glucopyranosyl chloride → Acetic acid (2S,3R,4S,4aR,10bR)-4-benzyloxy-3-ethynyl-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromen-2-ylmethyl ester + Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester (167646-56-2)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 4h; Ambient temperature; in presence of Bu₃SnCCSiMe₃;

DOI:10.1002/hlca.19960790423

Reference yield: 29.0%

(trimethylsilylethynyl)tributyltin (81353-38-0) + 6-O-acetyl-2,3-di-O-benzyl-4-deoxy-4-C-ethynyl-D-glucopyranosyl chloride → Acetic acid (2S,3R,4S,4aR,10bR)-4-benzyloxy-3-ethynyl-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromen-2-ylmethyl ester + Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester (167646-56-2)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1002/hlca.19960790423

Reference yield: 97.0%

Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester (167646-56-2) → ((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-ethynyl-6-trimethylsilanylethynyl-tetrahydro-pyran-2-yl)-methanol

Guidance literature:

With camphor-10-sulfonic acid; In methanol; for 10h; Heating;

DOI:10.1002/hlca.19960790423

upstream raw materials:

(trimethylsilylethynyl)tributyltin

Downstream raw materials:

3,3'-<(2,2'-bipyridine-6,6'-diyl)diethyne-2,1-diyl>bis<1-O-acetyl-2,6-anhydro-4,5-di-O-benzyl-3-deoxy-1-C-(trimethylsilyl)-D-glycero-L-gulo-oct-7-ynitol>

3,3'-<(2,2'-bipyridine-6,6'-diyl)diethyne-2,1-diyl>bis<2,6-anhydro-4,5-di-O-benzyl-3-deoxy-D-glycero-L-gulo-oct-7-ynitol>