benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside

Base Information

• Chemical Name: benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside
• CAS No.: 537036-60-5
• Molecular Formula: C₄₆H₅₂O₁₀
• Molecular Weight: 764.913
• Mol file: 537036-60-5.mol

Synonyms:benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside

Chemical Property of benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside

There total 1 articles about benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside 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: 74.0%

dimethyl (benzyl 2,3,4-tri-O-benzyl-α-D-manno-heptopyranos-6-ulos-7-yl)phosphonate (222417-79-0) + 2,2:4,5-di-O-isopropylidene-D-arabinose (13039-93-5) → benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside (537036-60-5)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In toluene; at 20 ℃; for 24h;

DOI:10.1016/S0008-6215(02)00484-6

Reference yield: 94.0%

benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside (537036-60-5) → benzyl 2,3,4-tri-O-benzyl-7,8-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-D-gluco-α-D-manno-dodeca-1,5-pyranoside (537036-61-6)

Guidance literature:

With zinc(II) tetrahydroborate; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1016/S0008-6215(02)00484-6

Reference yield:

benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside (537036-60-5) → benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside (106445-56-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 94 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

2.1: O₃ / CH₂Cl₂; methanol / -78 °C

2.2: NaBH₄ / 1 h / 20 °C

With zinc(II) tetrahydroborate; ozone; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0008-6215(02)00484-6

upstream raw materials:

dimethyl (benzyl 2,3,4-tri-O-benzyl-α-D-manno-heptopyranos-6-ulos-7-yl)phosphonate

2,2:4,5-di-O-isopropylidene-D-arabinose

Downstream raw materials:

benzyl 2,3,4-tri-O-benzyl-7,8-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-D-gluco-α-D-manno-dodeca-1,5-pyranoside

benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside

benzyl 2,3,4,6-tetra-O-benzyl-7,8-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-D-gluco-α-D-manno-dodeca-1,5-pyranoside