Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 225917-95-3
• Molecular Formula: C₂₈H₃₆O₁₆
• Molecular Weight: 628.584
• Mol file: 225917-95-3.mol

Synonyms:Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl 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: 82.0%

Benzoic acid (2R,3R,4S,5S,6S)-4-((3aR,5R,6R,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-3,5-dihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester → Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (225917-95-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1247::AID-ANIE1247>3.0.CO;2-J

Reference yield:

methyl 6-O-benzoyl-α-D-mannopyranoside (88087-59-6) → Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (225917-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / AgOTf; 2,4-lutidine; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

2: 82 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂

With 2,4-lutidine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; 1: Etherification / 2: Rearrangement;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1247::AID-ANIE1247>3.0.CO;2-J

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (225917-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / AgOTf; 2,4-lutidine; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

2: 82 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂

With 2,4-lutidine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; 1: Etherification / 2: Rearrangement;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1247::AID-ANIE1247>3.0.CO;2-J

upstream raw materials:

methyl 6-O-benzoyl-α-D-mannopyranoside

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide