1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone

Base Information

• Chemical Name: 1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone
• CAS No.: 528861-64-5
• Molecular Formula: C₃₃H₃₆O₇S
• Molecular Weight: 576.711
• Mol file: 528861-64-5.mol

Synonyms:1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone

Chemical Property of 1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone

There total 1 articles about 1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone 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: 86.0%

3-thiophthalimide-2,4-pentanedione (107552-89-6) + methyl 2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside (161016-86-0) → 1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone (528861-64-5)

Guidance literature:

With pyridine; at 60 ℃; for 93h;

DOI:10.1016/S0008-6215(02)00431-7

Reference yield: 53.0%

1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone (528861-64-5) → methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-3-hydroxymethyl-1,4-oxathiin

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1016/S0008-6215(02)00431-7

Reference yield: 32.0%

1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone (528861-64-5) → methyl 2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside (161016-86-0) + 4-{methyl (5S)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid-5-O-yl}pentan-2-one

Guidance literature:

With nickel; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1016/S0008-6215(02)00431-7

upstream raw materials:

3-thiophthalimide-2,4-pentanedione

methyl 2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside