Benzoic acid (2R,3S,4S,5R,6R)-2-{(2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-[2-(4-nitro-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R,6R)-2-{(2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-[2-(4-nitro-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 88261-78-3
• Molecular Formula: C₆₄H₆₅NO₁₅
• Molecular Weight: 1088.22

Synonyms:Benzoic acid (2R,3S,4S,5R,6R)-2-{(2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-[2-(4-nitro-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3S,4S,5R,6R)-2-{(2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-[2-(4-nitro-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3S,4S,5R,6R)-2-{(2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-[2-(4-nitro-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

There total 7 articles about Benzoic acid (2R,3S,4S,5R,6R)-2-{(2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-[2-(4-nitro-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-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: 70.0%

2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride (68536-53-8) + 2-(4-nitrophenyl)ethyl 2-O-acetyl-4,6-di-O-benzyl-α-D-mannopyranoside (88261-76-1) → Benzoic acid (2R,3S,4S,5R,6R)-2-{(2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-[2-(4-nitro-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (88261-78-3)

Guidance literature:

With silver(I) 4-methylbenzenesulfonate; In acetonitrile; for 43h; Ambient temperature;

DOI:10.1016/0008-6215(83)88407-9

Reference yield:

2-(4-nitrophenyl)ethanol (100-27-6) → Benzoic acid (2R,3S,4S,5R,6R)-2-{(2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-[2-(4-nitro-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (88261-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / silver p-toluenesulfonate / 6 h / Ambient temperature

2: 90 percent / NaOMe / methanol / 0.5 h / Ambient temperature

3: 78.7 percent / NaH, mercury(II) chloride / tetrahydrofuran

4: 70 percent / silver p-toluenesulfonate / acetonitrile / 43 h / Ambient temperature

With sodium methylate; silver(I) 4-methylbenzenesulfonate; sodium hydride; mercury dichloride; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1016/0008-6215(83)88407-9

Reference yield:

4,6-di-O-benzyl-D-mannopyranose → Benzoic acid (2R,3S,4S,5R,6R)-2-{(2S,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-[2-(4-nitro-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (88261-78-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 55 percent / pyridine / Ambient temperature

2: 86 percent / HCl / diethyl ether / 6 h / Ambient temperature

3: 82 percent / silver p-toluenesulfonate / 6 h / Ambient temperature

4: 90 percent / NaOMe / methanol / 0.5 h / Ambient temperature

5: 78.7 percent / NaH, mercury(II) chloride / tetrahydrofuran

6: 70 percent / silver p-toluenesulfonate / acetonitrile / 43 h / Ambient temperature

With pyridine; hydrogenchloride; sodium methylate; silver(I) 4-methylbenzenesulfonate; sodium hydride; mercury dichloride; In tetrahydrofuran; methanol; diethyl ether; acetonitrile;

DOI:10.1016/0008-6215(83)88407-9

upstream raw materials:

2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride

2-(4-nitrophenyl)ethyl 2-O-acetyl-4,6-di-O-benzyl-α-D-mannopyranoside

2-(4-nitrophenyl)ethanol

2,3-di-O-acetyl-4,6-di-O-benzyl-α-D-mannopyranosyl chloride

Downstream raw materials:

(2R,3S,4S,5S,6R)-2-{(2R,3R,4S,5S,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-[2-(4-isothiocyanato-phenyl)-ethoxy]-tetrahydro-pyran-4-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

2-(4-aminophenyl)ethyl 3-O-(α-D-mannopyranosyl)-α-D-mannopyranoside

2-(4-nitrophenyl)ethyl 4,6-di-O-benzyl-3-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside

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