Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-[(2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-(2-octylcarbamoyl-ethyl)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-[(2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-(2-octylcarbamoyl-ethyl)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 304466-75-9
• Molecular Formula: C₅₈H₇₃N₃O₁₇
• Molecular Weight: 1084.23

Synonyms:Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-[(2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-(2-octylcarbamoyl-ethyl)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-[(2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-(2-octylcarbamoyl-ethyl)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-[(2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-(2-octylcarbamoyl-ethyl)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-4-yl ester

There total 8 articles about Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-[(2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-(2-octylcarbamoyl-ethyl)-tetrahydro-pyran-2-ylmethoxy]-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: 98.0%

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) + 1-N-octyl-3-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)propionamide (213895-87-5) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-[(2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-(2-octylcarbamoyl-ethyl)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-4-yl ester (304466-75-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -42 ℃; for 6h;

DOI:10.1021/ja001224k

Reference yield:

3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene (82659-55-0) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-[(2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-(2-octylcarbamoyl-ethyl)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-4-yl ester (304466-75-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 9-BBN / tetrahydrofuran / 2.5 h / Heating

1.2: 90 percent / H₂O₂; 4M aq. NaOH / ethanol / 12 h / 0 °C

2.1: 92 percent / CrO₃; aq. H₂SO₄ / acetone / 1.5 h / 20 °C

3.1: 61 percent / HOBt; EDCI / CH₂Cl₂ / 12 h / 20 °C

4.1: TMSOTf / CH₂Cl₂ / 3 h / -42 °C

5.1: NaOMe / methanol

6.1: 98 percent / BF₃*OEt₂ / CH₂Cl₂ / 6 h / -42 °C

With chromium(VI) oxide; 9-borabicyclo[3.3.1]nonane dimer; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; acetone; 1.1: hydroboration / 1.2: Oxidation / 2.1: Oxidation / 3.1: Condensation / 4.1: Acetoxylation / 5.1: Deacetylation / 6.1: glycosylation;

DOI:10.1021/ja001224k

Reference yield:

2-N-p-nitrobenzyloxycarbonyl-3,4,6-tri-O-acetyl-D-glucosamine → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-[(2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-(2-octylcarbamoyl-ethyl)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-4-yl ester (304466-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / K₂CO₃ / CH₂Cl₂

2: 98 percent / BF₃*OEt₂ / CH₂Cl₂ / 6 h / -42 °C

With boron trifluoride diethyl etherate; potassium carbonate; In dichloromethane; 1: Addition / 2: glycosylation;

DOI:10.1021/ja001224k

upstream raw materials:

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

1-N-octyl-3-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)propionamide

3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene

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

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