(3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Base Information

Chemical Name:(3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol
CAS No.:634180-92-0
Molecular Formula:C₂₇H₄₄O₇Si
Molecular Weight:508.728
Hs Code.:

Synonyms:(3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

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Chemical Property of (3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

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Technology Process of (3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

There total 1 articles about (3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 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: 84.0%

: 13154-24-0
triisopropylsilyl chloride

: 479623-59-1
α-D-glucopyranose 1,2-(pent-4-enyl orthobenzoate)

: 634180-92-0
(3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;
DOI:10.1002/chem.200304856

Reference yield: 91.0%

: 100-39-0
benzyl bromide

: 634180-92-0
(3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

: 634180-93-1
((3aR,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-ylmethoxy)-triisopropyl-silane

Guidance literature:: (3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Further stages.;
DOI:10.1002/chem.200304856

Reference yield:

: 634180-92-0
(3aR,5R,6S,7S,7aR)-2-Pent-4-enyloxy-2-phenyl-5-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

: ((3aR,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-yl)-methanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C

1.2: 91 percent / dimethylformamide; various solvent(s) / 1 h / 20 °C

2.1: 2,6-lutidine; TBAF / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/chem.200304856