Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester

Base Information

• Chemical Name: Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester
• CAS No.: 161147-43-9
• Molecular Formula: C₃₈H₄₁NO₈
• Molecular Weight: 639.745

Synonyms:Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester

Chemical Property of Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester

There total 14 articles about Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl 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:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester (161147-43-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-BuLi, MgBr₂ / 1.) hexane, Et₂O, -5 deg C, 30 min, 2.) -30 deg C to r.t.

2: 74 percent / Bu₄NF / tetrahydrofuran / 0.25 h / Ambient temperature

3: 77 percent / Ph₃P, Zn(N₃)2*2py, diisopropyl azodicarboxylate / toluene / 0.5 h / Ambient temperature

4: 1,3-propanedithiol, Et₃N / methanol / 24 h / 45 °C

5: pyridine / 3 h / Ambient temperature

6: OsO₄, aq. NaIO₄ / tetrahydrofuran / 5 h / 45 °C

7: CH₂Cl₂

With pyridine; 1.3-propanedithiol; sodium periodate; osmium(VIII) oxide; n-butyllithium; zinc azide * 2 pyridine; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; magnesium bromide; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jo00108a030

Reference yield:

methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside (103597-22-4) → Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester (161147-43-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 15 h / Ambient temperature

2: 93 percent / K₂CO₃ / methanol / 0.33 h / Ambient temperature

3: 77 percent / Ph₃P, Zn(N₃)2*2py, diisopropyl azodicarboxylate / toluene / 0.5 h / Ambient temperature

4: 1,3-propanedithiol, Et₃N / methanol / 24 h / 45 °C

5: pyridine / 3 h / Ambient temperature

6: OsO₄, aq. NaIO₄ / tetrahydrofuran / 5 h / 45 °C

7: CH₂Cl₂

With pyridine; 1.3-propanedithiol; sodium periodate; osmium(VIII) oxide; zinc azide * 2 pyridine; di-isopropyl azodicarboxylate; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jo00108a030

Reference yield:

methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-α-D-glycero-D-gluco-octopyranoside (103597-18-8) → Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester (161147-43-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / Ph₃P, Zn(N₃)2*2py, diisopropyl azodicarboxylate / toluene / 0.5 h / Ambient temperature

2: 1,3-propanedithiol, Et₃N / methanol / 24 h / 45 °C

3: pyridine / 3 h / Ambient temperature

4: OsO₄, aq. NaIO₄ / tetrahydrofuran / 5 h / 45 °C

5: CH₂Cl₂

With pyridine; 1.3-propanedithiol; sodium periodate; osmium(VIII) oxide; zinc azide * 2 pyridine; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jo00108a030

upstream raw materials:

phenyldiazomethane

(R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid

acetic anhydride

(R)-Amino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid benzyl ester

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