N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 162606-13-5
• Molecular Formula: C₅₀H₅₇NO₁₁
• Molecular Weight: 848.003

Synonyms:N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Chemical Property of N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

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Technology Process of N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

There total 14 articles about N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide 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:

Acetic acid (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-(acetyl-benzenesulfonyl-amino)-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester → N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (162606-13-5)

Guidance literature:

Acetic acid (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-(acetyl-benzenesulfonyl-amino)-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester; With Na naphthalenide; In tetrahydrofuran; at -78 ℃;

With sodium methylate; In methanol; at 45 ℃;

DOI:10.1021/ol036183m

Reference yield:

3,6-di-O-benzyl-D-glucal (145852-76-2) → N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (162606-13-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Dess-Martin periodinane; NaHCO₃; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

1.2: NaBH₄ / methanol; CH₂Cl₂ / -5 °C

1.3: NaH / dimethylformamide / 20 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / -55 °C

3.1: tetrahydrofuran / 0 °C

4.1: pyridine / 20 °C

5.1: MeOTf; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂

6.1: I(collidine)2ClO₄; 4 Angstroem molecular sieves / 0 °C

6.2: NaOMe / 20 °C

7.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

8.1: Na naphthalenide / tetrahydrofuran / -78 °C

8.2: NaOMe / methanol / 45 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; Na naphthalenide; 3,3-dimethyldioxirane; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ol036183m

Reference yield:

(4aS,8S,8aR)-8-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine → N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (162606-13-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / 0 °C

1.2: CuI / tetrahydrofuran / 0.33 h / -10 °C

1.3: aq. KOH; aq. H₂O₂ / tetrahydrofuran; methanol / 18 h / 20 °C

2.1: (n-Bu)2SnO / toluene / 2 h / Heating

2.2: TBAI; Et₃N / toluene / 18 h / Heating

3.1: AcOH / tetrahydrofuran; H₂O / 2 h / 45 °C

4.1: TEMPO; aq. NaHCO₃; aq. NaOCl / CH₂Cl₂ / 0.5 h / 0 °C

5.1: N,N-dimethylformamide dineopentyl acetal / xylene / 1 h / 20 - 150 °C

6.1: Dess-Martin periodinane; NaHCO₃; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

6.2: NaBH₄ / methanol; CH₂Cl₂ / -5 °C

6.3: NaH / dimethylformamide / 20 °C

7.1: dimethyldioxirane / CH₂Cl₂; acetone / -55 °C

8.1: tetrahydrofuran / 0 °C

9.1: pyridine / 20 °C

10.1: MeOTf; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂

11.1: I(collidine)2ClO₄; 4 Angstroem molecular sieves / 0 °C

11.2: NaOMe / 20 °C

12.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

13.1: Na naphthalenide / tetrahydrofuran / -78 °C

13.2: NaOMe / methanol / 45 °C

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 2,6-di-tert-butyl-4-methylpyridine; iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; Na naphthalenide; 3,3-dimethyldioxirane; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; N,N-dimethylformamide dineopentyl acetal; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; water; acetone; toluene; xylene;

DOI:10.1021/ol036183m

upstream raw materials:

3,4,6-tri-O-benzyl-D-galactal

benzyl bromide

1,2-anhydro-3,4,6-tri-O-benzyl-D-galactopyranose

3,6-di-O-benzyl-D-glucal

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