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

Base Information

• Chemical Name: 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
• CAS No.: 120567-13-7
• Molecular Formula: C₅₄H₅₇NO₁₂
• Molecular Weight: 912.046

Synonyms:

Chemical Property of 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

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-((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

There total 5 articles about 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 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:

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-((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 (120567-13-7)

Guidance literature:

Multi-step reaction with 4 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

With methanol; Amberlist 15; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic 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-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (120567-11-5) → 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 (120567-13-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: Ag₂O, KI / dimethylformamide

With Amberlist 15; toluene-4-sulfonic acid; potassium iodide; silver(l) oxide; In N,N-dimethyl-formamide;

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

Reference yield:

allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-6-O-benzyl-2-deoxy-2-phtalimido-β-D-glucopyranoside (107802-77-7) → 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 (120567-13-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe, MeOH

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

3: Ag₂O, KI / dimethylformamide

With methanol; Amberlist 15; sodium methylate; toluene-4-sulfonic acid; potassium iodide; silver(l) oxide; In N,N-dimethyl-formamide;

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

upstream raw materials:

benzyl bromide

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

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

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

Downstream raw materials:

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

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

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

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