Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 192188-37-7
• Molecular Formula: C₅₄H₅₈N₂O₁₇
• Molecular Weight: 1007.06

Synonyms:Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

There total 6 articles about Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-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: 79.0%

benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (67831-42-9) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester (192188-33-3) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (192188-37-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -30 - 0 ℃; for 2h;

DOI:10.1039/a700549k

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (192188-37-7)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOMe, Et₃N / methanol

2: pyridine / 16 h

3: BnNH₂ / tetrahydrofuran / 16 h

4: K₂CO₃ / CH₂Cl₂ / 7 h

5: 79 percent / BF₃*Et₂O, MS 4A / CH₂Cl₂ / 2 h / -30 - 0 °C

With pyridine; boron trifluoride diethyl etherate; sodium methylate; potassium carbonate; triethylamine; benzylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/a700549k

Reference yield:

((3R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid 4-nitro-benzyl ester → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (192188-37-7)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 16 h

2: BnNH₂ / tetrahydrofuran / 16 h

3: K₂CO₃ / CH₂Cl₂ / 7 h

4: 79 percent / BF₃*Et₂O, MS 4A / CH₂Cl₂ / 2 h / -30 - 0 °C

With pyridine; boron trifluoride diethyl etherate; potassium carbonate; benzylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/a700549k

upstream raw materials:

benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

(+)-D-glucosamine hydrochloride

2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine

Downstream raw materials:

[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-carbamic acid 4-nitro-benzyl ester

(2R,3S,4R,5R,6S)-5-Amino-2-hydroxymethyl-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4-diol

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