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

Base Information

• Chemical Name: methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranoside
• CAS No.: 137101-04-3
• Molecular Formula: C₁₆H₂₂O₄S
• Molecular Weight: 310.414
• Mol file: 137101-04-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-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:

methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-2-thio-α-L-altropyranoside (137101-00-9) + methyl iodide (74-88-4) → methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranoside (137101-04-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 0.5h;

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

Reference yield:

methyl 2,6-anhydro-4-O-benzyl-3-O-tetrahydropyranyl-2-thio-α-L-altropyranoside (137100-95-9) → methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranoside (137101-04-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / BF₃*OEt₂ / methanol / 0.5 h / 0 °C

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

3: 85 percent / diethyl ether / 1.5 h / -75 to -25 deg C

4: 1) NaH / 1) DMF, 0 deg C, 20 min, 2) 25 deg C, 15 min

With boron trifluoride diethyl etherate; 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-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranoside (137101-04-3)

Guidance literature:

Multi-step reaction with 6 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: 85 percent / diethyl ether / 1.5 h / -75 to -25 deg C

6: 1) NaH / 1) DMF, 0 deg C, 20 min, 2) 25 deg C, 15 min

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

upstream raw materials:

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

methyl iodide

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

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

Downstream raw materials:

erythromycin A N-oxide

erythromycin

(9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide

(9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide