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

Base Information

• Chemical Name: 2-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 120567-14-8
• Molecular Formula: C₅₁H₅₃NO₁₂
• Molecular Weight: 871.981

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 2-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-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:

benzyl bromide (100-39-0) → 2-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (120567-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Ag₂O, KI / dimethylformamide

2: trifluoroacetic acid, H₂O, tetrahydrofuran

With tetrahydrofuran; water; trifluoroacetic acid; potassium iodide; silver(l) oxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)80600-0

Reference yield:

allyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (107823-72-3) → 2-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (120567-14-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 64 percent / SnCl₂, AgOTf, MS₄A / CH₂Cl₂; toluene

2: NaOMe, MeOH

3: 1) TsOH; 2) Amberlist 15 / 1) DMF; 2) MeOH

4: Ag₂O, KI / dimethylformamide

5: trifluoroacetic acid, H₂O, tetrahydrofuran

With tetrahydrofuran; methanol; Amberlist 15; water; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; trifluoroacetic acid; potassium iodide; tin(ll) chloride; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)80600-0

Reference yield:

2-[(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-4-hydroxy-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (120567-12-6) → 2-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (120567-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Ag₂O, KI / dimethylformamide

2: trifluoroacetic acid, H₂O, tetrahydrofuran

With tetrahydrofuran; water; trifluoroacetic acid; potassium iodide; silver(l) oxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)80600-0

upstream raw materials:

2-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

benzyl bromide

allyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-[(2R,3R,4R,5S,6R)-2-Allyloxy-6-benzyloxymethyl-4-hydroxy-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Downstream raw materials:

Acetic acid (2S,3R,4R,5S,6R)-4-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5S,6R)-4,5-diacetoxy-3-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yl ester

Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-6-[(2R,3S,4R,5R,6R)-6-allyloxy-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester

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