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

Base Information

• Chemical Name: 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
• CAS No.: 120567-12-6
• Molecular Formula: C₃₃H₃₉NO₁₂
• Molecular Weight: 641.672

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 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

There total 4 articles about 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 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-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)

Guidance literature:

Multi-step reaction with 3 steps

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

2: NaOMe, MeOH

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

With methanol; Amberlist 15; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; tin(ll) chloride; In dichloromethane; toluene;

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

Reference yield:

2,3,4,6-tetra-O-acetyl-β-galactopyranosyl fluoride (4163-45-5) → 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)

Guidance literature:

Multi-step reaction with 3 steps

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

2: NaOMe, MeOH

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

With methanol; Amberlist 15; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; tin(ll) chloride; In dichloromethane; toluene;

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-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)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe, MeOH

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

With methanol; Amberlist 15; sodium methylate; toluene-4-sulfonic acid;

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

upstream raw materials:

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

2,2-dimethoxy-propane

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

allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-6-O-benzyl-2-deoxy-2-phtalimido-β-D-glucopyranoside

Downstream 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

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

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

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