(4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

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Chemical Name:(4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]
CAS No.:220172-59-8
Molecular Formula:C₄₇H₅₆O₁₀
Molecular Weight:780.956
Hs Code.:

Synonyms:(4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

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Chemical Property of (4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

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Technology Process of (4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

There total 6 articles about (4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl] 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: 95.0%

: 100-39-0
benzyl bromide

: 220172-58-7
(E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol

: 220172-59-8
(4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; 1.) 30 min, 2.) r.t., 3 h;
DOI:10.1039/a807190j

Reference yield:

: 13039-93-5
2,2:4,5-di-O-isopropylidene-D-arabinose

: 220172-59-8
(4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / benzene / Ambient temperature

2: 95 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

3: 95 percent / NaH / dimethylformamide / 1.) 30 min, 2.) r.t., 3 h

With zinc(II) tetrahydroborate; sodium hydride; In diethyl ether; N,N-dimethyl-formamide; benzene;
DOI:10.1039/a807190j

Reference yield:

: 55610-71-4
methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

: 220172-59-8
(4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 15 min

2: 90 percent / 18-crown-6, K₂CO₃ / toluene / 16 h / Ambient temperature

3: 95 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

4: 95 percent / NaH / dimethylformamide / 1.) 30 min, 2.) r.t., 3 h

With n-butyllithium; zinc(II) tetrahydroborate; 18-crown-6 ether; sodium hydride; potassium carbonate; In diethyl ether; N,N-dimethyl-formamide; toluene;
DOI:10.1039/a807190j