Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 72062-88-5
• Molecular Formula: C₁₅H₂₀O₇S
• Molecular Weight: 344.386
• Mol file: 72062-88-5.mol

Synonyms:Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

There total 2 articles about Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-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: 97.0%

methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside (18944-96-2) + methanesulfonyl chloride (124-63-0) → Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (72062-88-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; 15 min, 0 deg C; 15 min, 25 deg C;

DOI:10.1016/0008-6215(84)85014-4

Reference yield:

Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester (18933-64-7) → Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (72062-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Raney nickel W-5 / propan-2-ol / 12 h / Ambient temperature

2: 97 percent / triethylamine / tetrahydrofuran / 15 min, 0 deg C; 15 min, 25 deg C

With hydrogen; triethylamine; Raney nickel W-5; In tetrahydrofuran; isopropyl alcohol;

DOI:10.1016/0008-6215(84)85014-4

Reference yield:

Benzoic acid (2R,3R,4R,6S)-4-methanesulfonyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (72062-88-5) → methyl 3-(N-benzyloxycarbonylamino)-2,3,6-trideoxy-α-D-arabino-hexopyranoside (83532-10-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium methoxide; 2.) sodium azide, ammonium chloride / 1.) MeOH, r.t., 5 h; 2.) reflux, 24 h

2: 86 percent / H₂ / PtO₂ / tetrahydrofuran / 6 h / Ambient temperature

3: 64 percent / NaHCO₃ / CH₂Cl₂ / 0.5 h / 25 °C

With sodium azide; ammonium chloride; hydrogen; sodium methylate; sodium hydrogencarbonate; platinum(IV) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0008-6215(84)85014-4

upstream raw materials:

methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside

methanesulfonyl chloride

Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

Downstream raw materials:

methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside

methyl 3-(N-benzyloxycarbonylamino)-2,3,6-trideoxy-α-D-arabino-hexopyranoside

methyl 3-(benzyloxycarbonyl)amino-2,3,6-trideoxy-α-arabino-hexopyranosid-4-ulose