(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid methyl ester

Base Information

• Chemical Name: (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid methyl ester
• CAS No.: 695177-57-2
• Molecular Formula: C₆₆H₇₈N₂O₁₅
• Molecular Weight: 1139.35

Synonyms:

Chemical Property of (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid methyl ester

There total 7 articles about (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid methyl 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:

O-(2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate (130177-78-5) → (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid methyl ester (695177-57-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 75 percent / Sn(OTf)2 / CH₂Cl₂; acetonitrile / 0.17 h / -20 °C

2.1: TBAF / tetrahydrofuran

3.1: NaOMe / methanol

4.1: NaH / dimethylformamide

5.1: HNO₃; Ac₂O

5.2: 75 percent / Et₃N / CH₂Cl₂

6.1: 77 percent / t-BuOK / toluene

7.1: Zn; aq. HCl; AcOH / tetrahydrofuran / 2 h / 0 °C

8.1: pyridine

With pyridine; hydrogenchloride; tin(II) trifluoromethanesulfonate; potassium tert-butylate; tetrabutyl ammonium fluoride; nitric acid; sodium methylate; acetic anhydride; sodium hydride; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Michael addition;

DOI:10.1055/s-2004-817790

Reference yield:

1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol (166021-01-8) → (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid methyl ester (695177-57-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 75 percent / Sn(OTf)2 / CH₂Cl₂; acetonitrile / 0.17 h / -20 °C

2.1: TBAF / tetrahydrofuran

3.1: NaOMe / methanol

4.1: NaH / dimethylformamide

5.1: HNO₃; Ac₂O

5.2: 75 percent / Et₃N / CH₂Cl₂

6.1: 77 percent / t-BuOK / toluene

7.1: Zn; aq. HCl; AcOH / tetrahydrofuran / 2 h / 0 °C

8.1: pyridine

With pyridine; hydrogenchloride; tin(II) trifluoromethanesulfonate; potassium tert-butylate; tetrabutyl ammonium fluoride; nitric acid; sodium methylate; acetic anhydride; sodium hydride; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Michael addition;

DOI:10.1055/s-2004-817790

Reference yield:

(2R,3R,4R)-3-Benzyloxy-2-benzyloxymethyl-5-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran (365455-39-6) → (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid methyl ester (695177-57-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / t-BuOK / toluene

2: Zn; aq. HCl; AcOH / tetrahydrofuran / 2 h / 0 °C

3: pyridine

With pyridine; hydrogenchloride; potassium tert-butylate; acetic acid; zinc; In tetrahydrofuran; toluene; 1: Michael addition;

DOI:10.1055/s-2004-817790

upstream raw materials:

O-(2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate

1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol

(2R,3R,4R)-3-Benzyloxy-2-benzyloxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran

(2R,3R,4R)-3-Benzyloxy-2-benzyloxymethyl-5-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran

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