(2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran
• CAS No.: 607715-91-3
• Molecular Formula: C₃₅H₃₅IO₅
• Molecular Weight: 662.564
• Mol file: 607715-91-3.mol

Synonyms:(2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran

Chemical Property of (2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran

There total 2 articles about (2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran 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: 72.0%

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one (179090-11-0) → (2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran (607715-91-3)

Guidance literature:

With iodonium di(2,4,6-collidinium) triflate; In dichloromethane;

DOI:10.1016/S0040-4039(03)01455-2

Reference yield:

2,3,4,6-tetra-O-benzyl-D-galactonolactone (82598-84-3) → (2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran (607715-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / toluene

2: 72 percent / iodonium dicollidinium triflate / CH₂Cl₂

With iodonium di(2,4,6-collidinium) triflate; In dichloromethane; toluene;

DOI:10.1016/S0040-4039(03)01455-2

Reference yield: 92.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + (2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran (607715-91-3) → (2R,3R,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran (1462962-14-6)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; tetrabutyl-ammonium chloride; palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

DOI:10.1016/j.tetlet.2013.08.118

upstream raw materials:

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one

2,3,4,6-tetra-O-benzyl-D-galactonolactone

Downstream raw materials:

C₄₇H₅₆O₅

(2R,3R,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran

(2R,3S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)-3,6-dihydro-2H-pyran

(2R,3S,6S)-3-((tert-butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-((Z)-((3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ylidene)methyl)dihydro-2H-pyran-4(3H)-one