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

Base Information

• Chemical Name: Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 93960-50-0
• Molecular Formula: C₁₄H₁₇BrO₅
• Molecular Weight: 345.19
• Mol file: 93960-50-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-3-hydroxy-6-methoxy-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:

methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside (6752-48-3,16718-95-9,18424-62-9,19877-02-2,22886-97-1,52153-29-4,52612-68-7,55331-65-2,64978-95-6,65725-24-8,66512-93-4,67968-51-8,72904-80-4,77481-69-7,131615-73-1,138663-49-7,151214-39-0) → Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (93960-50-0)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In dimethyl sulfoxide;

DOI:10.1002/1521-3773(20010202)40:3<607::AID-ANIE607>3.0.CO;2-8

Reference yield:

Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (93960-50-0) → C23H28F2N2O14P2

Guidance literature:

Multi-step reaction with 7 steps

1.1: Bu₃SnH; AIBN / benzene

2.1: 69 percent / pyridinium chlorochromate / CH₂Cl₂

3.1: 82 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂

4.1: 85 percent / Dowex-50W(H⁺) / acetonitrile; H₂O

5.1: BuLi / tetrahydrofuran

5.2: 66 percent / tetrahydrofuran

6.1: 93 percent / H₂ / Pd/C / methanol

7.1: 1H-tetrazole; pyridine

With pyridine; 1H-tetrazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); diethylamino-sulfur trifluoride; Dowex-50W(H⁺); hydrogen; tri-n-butyl-tin hydride; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; benzene;

DOI:10.1002/1521-3773(20010202)40:3<607::AID-ANIE607>3.0.CO;2-8

Reference yield:

Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (93960-50-0) → Benzoic acid (2R,4S,6R)-3,3-difluoro-2-methyl-6-phosphonooxy-tetrahydro-pyran-4-yl ester

Guidance literature:

Multi-step reaction with 6 steps

1.1: Bu₃SnH; AIBN / benzene

2.1: 69 percent / pyridinium chlorochromate / CH₂Cl₂

3.1: 82 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂

4.1: 85 percent / Dowex-50W(H⁺) / acetonitrile; H₂O

5.1: BuLi / tetrahydrofuran

5.2: 66 percent / tetrahydrofuran

6.1: 93 percent / H₂ / Pd/C / methanol

With n-butyllithium; 2,2'-azobis(isobutyronitrile); diethylamino-sulfur trifluoride; Dowex-50W(H⁺); hydrogen; tri-n-butyl-tin hydride; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; benzene;

DOI:10.1002/1521-3773(20010202)40:3<607::AID-ANIE607>3.0.CO;2-8

upstream raw materials:

methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside

Downstream raw materials:

methyl 3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside

methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose