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

Base Information

• Chemical Name: 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
• CAS No.: 120567-15-9
• Molecular Formula: C₅₅H₅₇NO₁₄
• Molecular Weight: 956.056

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 8 articles about 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 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) → 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 (120567-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Ag₂O, KI / dimethylformamide

2: trifluoroacetic acid, H₂O, tetrahydrofuran

3: dimethylaminopropylamine / pyridine

With tetrahydrofuran; water; 1-amino-3-(dimethylamino)propane; trifluoroacetic acid; potassium iodide; silver(l) oxide; In pyridine; 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) → 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 (120567-15-9)

Guidance literature:

Multi-step reaction with 6 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

6: dimethylaminopropylamine / pyridine

With tetrahydrofuran; methanol; Amberlist 15; water; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; 1-amino-3-(dimethylamino)propane; trifluoroacetic acid; potassium iodide; tin(ll) chloride; silver(l) oxide; In pyridine; 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) → 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 (120567-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Ag₂O, KI / dimethylformamide

2: trifluoroacetic acid, H₂O, tetrahydrofuran

3: dimethylaminopropylamine / pyridine

With tetrahydrofuran; water; 1-amino-3-(dimethylamino)propane; trifluoroacetic acid; potassium iodide; silver(l) oxide; In pyridine; N,N-dimethyl-formamide;

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

upstream raw materials:

acetic anhydride

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

benzyl bromide

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

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

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