2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

Chemical Name:2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
CAS No.:351209-68-2
Molecular Formula:C₆₀H₆₃NO₁₁S
Molecular Weight:1006.23
Hs Code.:

2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Synonyms:2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

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Chemical Property of 2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

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Technology Process of 2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 8 articles about 2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 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: 99.0%

: 895140-70-2
(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-ylamine

: 85-44-9
phthalic anhydride

: 351209-68-2
2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Guidance literature:: (2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-ylamine; phthalic anhydride; With pyridine; at 20 ℃; for 0.75h;

With 2,2-dimethylpropanoic anhydride; at 85 ℃; for 120h;
DOI:10.1016/j.tet.2006.02.080

Reference yield:

: 51450-24-9
hexa-O-acetyl-D-lactal

: 351209-68-2
2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: NH₃ / methanol

2.1: Bu₂SnO / benzene

2.2: Bu₄NBr

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 91 percent / dimethylformamide / 24 h / 20 °C

4.1: CH₂Cl₂ / 0.5 h / 20 °C

4.2: 75 percent / I₂; Ag(collidine)2ClO₄ / CH₂Cl₂ / 1.5 h / 0 °C

5.1: 85 percent / LiHMDS / dimethylformamide; tetrahydrofuran / -40 - 20 °C

6.1: 94 percent / CsF / dimethylformamide / 48 h / 90 °C

7.1: pyridine / 0.75 h / 20 °C

7.2: 99 percent / pivalic anhydride / 120 h / 85 °C

With pyridine; ammonia; sodium hydride; di(n-butyl)tin oxide; cesium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.tet.2006.02.080

Reference yield:

: 2-Trimethylsilanyl-ethanesulfonic acid [(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-iodo-tetrahydro-pyran-3-yl]-amide

: 351209-68-2
2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / LiHMDS / dimethylformamide; tetrahydrofuran / -40 - 20 °C

2.1: 94 percent / CsF / dimethylformamide / 48 h / 90 °C

3.1: pyridine / 0.75 h / 20 °C

3.2: 99 percent / pivalic anhydride / 120 h / 85 °C

With pyridine; cesium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2006.02.080