methyl 2,6-anhydro-4-O-benzyl-2-thio-α-L-arabino-hexopyranosid-3-ulose

Base Information

• Chemical Name: methyl 2,6-anhydro-4-O-benzyl-2-thio-α-L-arabino-hexopyranosid-3-ulose
• CAS No.: 137100-98-2
• Molecular Formula: C₁₄H₁₆O₄S
• Molecular Weight: 280.345
• Mol file: 137100-98-2.mol

Synonyms:methyl 2,6-anhydro-4-O-benzyl-2-thio-α-L-arabino-hexopyranosid-3-ulose

Chemical Property of methyl 2,6-anhydro-4-O-benzyl-2-thio-α-L-arabino-hexopyranosid-3-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,6-anhydro-4-O-benzyl-2-thio-α-L-arabino-hexopyranosid-3-ulose

There total 5 articles about methyl 2,6-anhydro-4-O-benzyl-2-thio-α-L-arabino-hexopyranosid-3-ulose 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 2,6-anhydro-4-O-benzyl-2-thio-α-L-altropyranoside (137100-96-0) → methyl 2,6-anhydro-4-O-benzyl-2-thio-α-L-arabino-hexopyranosid-3-ulose (137100-98-2)

Guidance literature:

With Dess-Martin periodane;

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-2-thio-α-L-arabino-hexopyranosid-3-ulose (137100-98-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With boron trifluoride diethyl etherate; Dess-Martin periodane; In methanol; 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-arabino-hexopyranosid-3-ulose (137100-98-2)

Guidance literature:

Multi-step reaction with 4 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

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

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

upstream raw materials:

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

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

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-methyl-2-thio-α-L-altropyranoside

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

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

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