Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside

Base Information

• Chemical Name: Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside
• CAS No.: 76491-21-9
• Molecular Formula: C₂₈H₃₁IO₅
• Molecular Weight: 574.456
• Mol file: 76491-21-9.mol

Synonyms:Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside

Chemical Property of Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside

There total 1 articles about Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside 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: 87.0%

(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol (20672-67-7,40246-25-1,40246-30-8,73415-91-5,73445-27-9,81086-90-0,148888-64-6) → Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside (76491-21-9)

Guidance literature:

With tri-iodoimidazole; triphenylphosphine; In toluene; for 6h; Heating;

Reference yield: 23.0%

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside (76491-21-9) → 1-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-2,2,6,6-tetramethyl-piperidine + 1-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-2,2,6,6-tetramethyl-piperidine

Guidance literature:

With bis(tri-n-butyltin); In benzene; at 40 ℃; for 2h; Irradiation;

DOI:10.1039/c39940000837

Reference yield:

Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside (76491-21-9) → methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (20672-67-7) + (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol (20672-67-7,40246-25-1,40246-30-8,73415-91-5,73445-27-9,81086-90-0,148888-64-6)

Guidance literature:

With air; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 60 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0040-4039(94)88272-X

upstream raw materials:

(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol

Downstream raw materials:

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol