(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid
• CAS No.: 213913-15-6
• Molecular Formula: C₅₁H₄₉NO₁₈
• Molecular Weight: 963.946

Synonyms:

Chemical Property of (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid

There total 15 articles about (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid 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:

C51H49NO17 → (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid (213913-15-6)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In water; tert-butyl alcohol; Yield given;

DOI:10.1016/S0008-6215(98)00125-6

Reference yield:

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid (213913-15-6)

Guidance literature:

Multi-step reaction with 17 steps

1: NaOMe / methanol / 8 h / pH 10

2: pyridine / 4.5 h / 0 °C

3: pyridine / Ambient temperature

4: p-toluenesulfonic acid / acetonitrile; H₂O / 5 h / pH 3

5: 2-chloro-1-methylpyridinium iodide, 1,4-diazabicyclo<2.2.2>octane / 1,2-dichloro-ethane / 0.33 h

6: 88 percent / ammonium cerium(IV) nitrate / toluene; acetonitrile; H₂O / 0.5 h

7: 89 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂

8: 89 percent / 4 Angstroem molecular sieves, Me₃SiOTf / CH₂Cl₂ / 0.17 h

9: 98 percent / CF₃CO₂H / CH₂Cl₂; H₂O / 0.5 h

10: 96 percent / pyridine / 6 h / 0 °C

11: CH₂Cl₂; pyridine / 6 h / 0 °C

12: dimethylformamide / Ambient temperature

13: 91 percent / p-toluenesulfonic acid / acetonitrile; H₂O / 2 h

14: 88 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

15: 94 percent / hydrazinium acetate / ethanol; toluene / 1.5 h

16: 1.) oxalyl chloride, methyl sulfoxide, 2.) diisopropylethylamine / 1.) CH₂Cl₂, 1 h, 2.) CH₂Cl₂, 10 min

17: NaClO₂, NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s); H₂O

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 2-chloro-1-methyl-pyridinium iodide; sodium methylate; hydrazinium monoacetate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In pyridine; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0008-6215(98)00125-6

Reference yield:

6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate (144367-26-0) → (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid (213913-15-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 89 percent / 4 Angstroem molecular sieves, Me₃SiOTf / CH₂Cl₂ / 0.17 h

2: 98 percent / CF₃CO₂H / CH₂Cl₂; H₂O / 0.5 h

3: 96 percent / pyridine / 6 h / 0 °C

4: CH₂Cl₂; pyridine / 6 h / 0 °C

5: dimethylformamide / Ambient temperature

6: 91 percent / p-toluenesulfonic acid / acetonitrile; H₂O / 2 h

7: 88 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

8: 94 percent / hydrazinium acetate / ethanol; toluene / 1.5 h

9: 1.) oxalyl chloride, methyl sulfoxide, 2.) diisopropylethylamine / 1.) CH₂Cl₂, 1 h, 2.) CH₂Cl₂, 10 min

10: NaClO₂, NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s); H₂O

With dmap; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrazinium monoacetate; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0008-6215(98)00125-6

upstream raw materials:

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

4-methoxyphenyl 6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranoside

6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate

allyl (6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranoside

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