methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate

Base Information

• Chemical Name: methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate
• CAS No.: 666238-73-9
• Molecular Formula: C₂₈H₃₂O₁₀
• Molecular Weight: 528.556
• Mol file: 666238-73-9.mol

Synonyms:methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate

Chemical Property of methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate

There total 16 articles about methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate 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: 71.0%

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) + methyl (2-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyl)uronate trichloroacetimidate (666238-37-5) → methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate (666238-73-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 2h;

DOI:10.1081/CAR-120026603

Reference yield: 69.0%

(5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactone (78158-90-4) + methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranuronate (666238-16-0) → methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate (666238-73-9)

Guidance literature:

(5R)-5-<(triphenylmethoxy)methyl>-γ-butyrolactone; methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranuronate; In dichloromethane;

With triphenylmethyl perchlorate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1081/CAR-120026603

Reference yield: 45.0%

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) + methyl 2-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyluronate bromide (666238-29-5) → methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate (666238-73-9)

Guidance literature:

methyl 2-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyluronate bromide; With silver perchlorate; In acetonitrile; at -15 ℃; for 0.666667h;

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1081/CAR-120026603

upstream raw materials:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

methyl 2-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyluronate bromide

methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranuronate

methyl (2-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyl)uronate trichloroacetimidate

Downstream raw materials:

(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosiduronic acid

methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 3,4-di-O-benzyl-β-D-glucopyranosid]uronate