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

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol
• CAS No.: 131603-37-7
• Molecular Formula: C₃₅H₃₇IO₆
• Molecular Weight: 680.58

Synonyms:(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol

Chemical Property of (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol

Chemical Property:

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Technology Process of (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol

There total 2 articles about (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol 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: 46.0%

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + diiodomethane (75-11-6) → 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranose (137344-41-3) + (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol (131603-37-7)

Guidance literature:

With methyllithium; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;

DOI:10.1016/j.tetlet.2011.12.049

Reference yield:

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (133697-34-4,97321-70-5) → (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol (131603-37-7)

Guidance literature:

With N-iodo-succinimide; In water;

DOI:10.1016/S0040-4039(97)00327-4

Reference yield: 73.0%

(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol (131603-37-7) → 1-deoxy-1-amino-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose (1357160-41-8)

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; at 20 ℃; for 4.5h;

DOI:10.1016/j.tetlet.2011.12.049

upstream raw materials:

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

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

diiodomethane

Downstream raw materials:

1,6-anhydro-2,3,4-trideoxy-4-C-(3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranos-1-yl)-D-glycero-hexo-pyranos-2-ulose

(Z)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-(2-pyridylamino)-D-gluco-hept-1-enitol

1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

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