(2S,3S,4R,5S)-2-((2S,3S,4R,5R)-4-(benzoyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(2-phenyl-1,3-dioxan-5-yloxy)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)-4-(benzoyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(2-phenyl-1,3-dioxan-5-yloxy)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate
CAS No.:1612138-69-8
Molecular Formula:C₆₀H₅₆O₁₈
Molecular Weight:1065.09
Hs Code.:

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

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

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

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

There total 15 articles about (2S,3S,4R,5S)-2-((2S,3S,4R,5R)-4-(benzoyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(2-phenyl-1,3-dioxan-5-yloxy)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: 67.0%

: 1033560-31-4
4-methylphenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside

: 1612138-71-2
(2R,3S,4R,5R)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2-(2-phenyl-1,3-dioxan-5-yloxy)tetrahydrofuran-3-yl benzoate

: 1612138-69-8
(2S,3S,4R,5S)-2-((2S,3S,4R,5R)-4-(benzoyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(2-phenyl-1,3-dioxan-5-yloxy)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate

Guidance literature:: 4-methylphenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside; (2R,3S,4R,5R)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2-(2-phenyl-1,3-dioxan-5-yloxy)tetrahydrofuran-3-yl benzoate; With N-iodo-succinimide; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 4h; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.tet.2014.04.069

Reference yield:

: 1611470-12-2
C₅₂H₄₆Cl₃NO₁₆

: 1708-40-3
2-phenyl-[1,3]dioxan-5-ol

: 1612138-69-8
(2S,3S,4R,5S)-2-((2S,3S,4R,5R)-4-(benzoyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(2-phenyl-1,3-dioxan-5-yloxy)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.tet.2014.04.069

Reference yield:

: 920267-56-7
4-methylphenyl 1-thio-β-D-galactofuranoside

: 1612138-69-8
(2S,3S,4R,5S)-2-((2S,3S,4R,5R)-4-(benzoyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(2-phenyl-1,3-dioxan-5-yloxy)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: (1S)-10-camphorsulfonic acid / dichloromethane / 2 h / 20 °C

2.1: 1H-imidazole; dmap / dichloromethane / 0 - 20 °C

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 °C / Molecular sieve

4.1: N-iodo-succinimide / dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

4.2: 4 h / 0 °C / Molecular sieve; Inert atmosphere

With 1H-imidazole; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; In dichloromethane;
DOI:10.1016/j.tet.2014.04.069