methyl 2-S-benzoyl-4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-tetrahydropyranyl-α-L-altropyranoside

Base Information

• Chemical Name: methyl 2-S-benzoyl-4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-tetrahydropyranyl-α-L-altropyranoside
• CAS No.: 137100-93-7
• Molecular Formula: C₂₆H₂₉BrO₇S
• Molecular Weight: 565.482
• Mol file: 137100-93-7.mol

Synonyms:methyl 2-S-benzoyl-4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-tetrahydropyranyl-α-L-altropyranoside

Chemical Property of methyl 2-S-benzoyl-4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-tetrahydropyranyl-α-L-altropyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-S-benzoyl-4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-tetrahydropyranyl-α-L-altropyranoside

There total 1 articles about methyl 2-S-benzoyl-4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-tetrahydropyranyl-α-L-altropyranoside 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%

3,4-dihydro-2H-pyran (110-87-2) + Benzoic acid (2R,3R,4S,5R,6R)-5-benzoylsulfanyl-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester (137100-92-6) → methyl 2-S-benzoyl-4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-tetrahydropyranyl-α-L-altropyranoside (137100-93-7)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)79886-8

Reference yield:

methyl 2-S-benzoyl-4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-tetrahydropyranyl-α-L-altropyranoside (137100-93-7) → (1R,3R,4R,7S,8R)-7-Benzyloxy-3-methoxy-8-methyl-2-oxa-5-thia-bicyclo[2.2.2]octan-8-ol (137101-01-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / NaOMe / methanol / 3 h / 25 °C

2: 1) NaH / 1) DMF, 0 deg C, 1h, 2) 25 deg C, 1h

3: 97 percent / BF₃*OEt₂ / methanol / 0.5 h / 0 °C

4: 97 percent / periodinane / CH₂Cl₂ / 2 h / 25 °C

5: 9 percent / diethyl ether / 1.5 h / -75 to -25 deg C

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; Dess-Martin periodane; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/0008-6215(91)89016-9

Reference yield:

methyl 2-S-benzoyl-4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-tetrahydropyranyl-α-L-altropyranoside (137100-93-7) → methyl 2,6-anhydro-4-O-benzyl-2-thio-α-L-altropyranoside (137100-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / NaOMe / methanol / 3 h / 25 °C

2: 1) NaH / 1) DMF, 0 deg C, 1h, 2) 25 deg C, 1h

3: 97 percent / BF₃*OEt₂ / methanol / 0.5 h / 0 °C

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In methanol;

DOI:10.1016/0008-6215(91)89016-9

upstream raw materials:

3,4-dihydro-2H-pyran

Benzoic acid (2R,3R,4S,5R,6R)-5-benzoylsulfanyl-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

Downstream raw materials:

methyl 2,6-anhydro-4-O-benzyl-3-O-tetrahydropyranyl-2-thio-α-L-altropyranoside

methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-2-thio-α-L-altropyranoside

(1R,3R,4R,7S,8R)-7-Benzyloxy-3-methoxy-8-methyl-2-oxa-5-thia-bicyclo[2.2.2]octan-8-ol

methyl 2,6-anhydro-4-O-benzyl-2-thio-α-L-altropyranoside