methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside

Base Information

• Chemical Name: methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside
• CAS No.: 402758-95-6
• Molecular Formula: C₇₄H₈₂O₁₃Si
• Molecular Weight: 1207.54
• Mol file: 402758-95-6.mol

Synonyms:methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside

Chemical Property of methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside

There total 12 articles about methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside 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: 63.0%

p-cresyl 2,3,5-tri-O-benzyl-1-thio-D-arabinofuranoside (278796-50-2) + methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside (402758-94-5) → methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside (402758-95-6)

Guidance literature:

With N-iodo-succinimide; molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -78 - 0 ℃; for 3h;

DOI:10.1021/jo010910e

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside (402758-95-6)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP / pyridine / 4 h / 0 °C

2: 92 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

3: 63 percent / molecular sieves; NIS; AgOTf / CH₂Cl₂ / 3 h / -78 - 0 °C

With dmap; N-iodo-succinimide; molecular sieve; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; In pyridine; dichloromethane;

DOI:10.1021/jo010910e

Reference yield:

benzyl bromide (100-39-0) → methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside (402758-95-6)

Guidance literature:

Multi-step reaction with 6 steps

1: NaH / dimethylformamide / 2 h / 0 °C

2: 580 mg / n-Bu₄NF / tetrahydrofuran / 20 °C

3: 76 percent / pyridine / 24 h / 20 °C

4: 60 percent / molecular sieves; NIS; AgOTf / CH₂Cl₂ / 0 °C

5: 68 percent / NaOCH₃ / methanol / 2 h / 20 °C

6: 63 percent / molecular sieves; NIS; AgOTf / CH₂Cl₂ / 3 h / -78 - 0 °C

With N-iodo-succinimide; molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Zemplen deacylation;

DOI:10.1021/jo010910e

upstream raw materials:

p-cresyl 2,3,5-tri-O-benzyl-1-thio-D-arabinofuranoside

methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside

2,3,5-tri-O-benzyl-D-arabinofuranose

benzyl bromide