(2S,3S,4R,5S)-2-((2S,3S,4R,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate

Base Information

• Chemical Name: (2S,3S,4R,5S)-2-((2S,3S,4R,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate
• CAS No.: 1611470-09-7
• Molecular Formula: C₆₆H₆₆O₁₅Si
• Molecular Weight: 1127.33
• Mol file: 1611470-09-7.mol

Synonyms:(2S,3S,4R,5S)-2-((2S,3S,4R,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate

Chemical Property of (2S,3S,4R,5S)-2-((2S,3S,4R,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5S)-2-((2S,3S,4R,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate

There total 1 articles about (2S,3S,4R,5S)-2-((2S,3S,4R,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate 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: 64.0%

4-methylphenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside (1033560-31-4) + (2R,3R,4S,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-ol → (2S,3S,4R,5S)-2-((2S,3S,4R,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate (1611470-09-7)

Guidance literature:

4-methylphenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside; (2R,3R,4S,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-ol; With N-iodo-succinimide; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve;

With silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 4h; Molecular sieve;

DOI:10.1016/j.tet.2014.04.069

Reference yield:

(2S,3S,4R,5S)-2-((2S,3S,4R,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate (1611470-09-7) → C22H32O11

Guidance literature:

With tetrabutyl ammonium fluoride; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2014.04.069

upstream raw materials:

4-methylphenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside