benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-anhydro-β-D-ribopyranoside

Base Information

• Chemical Name: benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-anhydro-β-D-ribopyranoside
• CAS No.: 125325-75-9
• Molecular Formula: C₄₆H₄₈O₉
• Molecular Weight: 744.882
• Mol file: 125325-75-9.mol

Synonyms:benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-anhydro-β-D-ribopyranoside

Chemical Property of benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-anhydro-β-D-ribopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-anhydro-β-D-ribopyranoside

There total 3 articles about benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-anhydro-β-D-ribopyranoside 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: 96.0%

(-)-benzyl 2,3-anhydro-β-D-ribopyranoside (67412-71-9) + 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl diethyl phosphite (193953-69-4) → benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-anhydro-β-D-ribopyranoside (125325-75-9)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/0040-4039(95)00263-C

Reference yield: 82.0%

(-)-benzyl 2,3-anhydro-β-D-ribopyranoside (67412-71-9) + C53H52NO8PS (130948-37-7) → (1R,2R,5R,6R)-2-Benzyloxy-5-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,7-dioxa-bicyclo[4.1.0]heptane (125325-75-9,130738-61-3,143520-23-4,143520-24-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -55 ℃; for 0.5h;

DOI:10.1248/cpb.38.2323

Reference yield:

(-)-benzyl 2,3-anhydro-β-D-ribopyranoside (67412-71-9) + S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-N,N,N',N'-tetramethyl-N''-phenylphosphorodiamidimidothioate (166733-02-4) → benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3-anhydro-β-D-ribopyranoside (130738-61-3) + benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-anhydro-β-D-ribopyranoside (125325-75-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; 2,6-lutidinium p-toluenesulfonate; 4 A molecular sieve; In toluene; at 23 ℃; for 55h; Yield given. Yields of byproduct given; further reaction conditions;

DOI:10.1016/S0040-4039(00)97729-3

upstream raw materials:

(-)-benzyl 2,3-anhydro-β-D-ribopyranoside

S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-N,N,N',N'-tetramethyl-N''-phenylphosphorodiamidimidothioate

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl diethyl phosphite

C₅₃H₅₂NO₈PS