(1R,2R,3S,4R)-2,3,4-tri-O-benzyl-1-O-pivaloyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

Base Information

• Chemical Name: (1R,2R,3S,4R)-2,3,4-tri-O-benzyl-1-O-pivaloyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol
• CAS No.: 866336-50-7
• Molecular Formula: C₄₀H₄₄O₆
• Molecular Weight: 620.786
• Mol file: 866336-50-7.mol

Synonyms:(1R,2R,3S,4R)-2,3,4-tri-O-benzyl-1-O-pivaloyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

Chemical Property of (1R,2R,3S,4R)-2,3,4-tri-O-benzyl-1-O-pivaloyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4R)-2,3,4-tri-O-benzyl-1-O-pivaloyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

There total 2 articles about (1R,2R,3S,4R)-2,3,4-tri-O-benzyl-1-O-pivaloyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol 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: 65.0%

(3R,4S,5S,6R)-1,3,4,5-tetra-O-benzyl-6-O-pivaloyl-2-methylene-oct-7-ene-1,3,4,5,6-pentaol (866336-49-4) → (1R,2R,3S,4R)-2,3,4-tri-O-benzyl-1-O-pivaloyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol (866336-50-7)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 60 ℃;

DOI:10.1016/j.tetlet.2005.07.054

Reference yield:

(3R,4S,5S,6R)-1,3,4,5-tetra-O-benzyl-6-O-pivaloyl-1,3,4,5,6-pentahydroxy-oct-7-en-2-one (866336-48-3) → (1R,2R,3S,4R)-2,3,4-tri-O-benzyl-1-O-pivaloyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol (866336-50-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / NaHMDS / tetrahydrofuran / -78 °C

2: 65 percent / Grubbs'second generation catalyst / toluene / 60 °C

With sodium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; toluene; 1: Wittig olefination;

DOI:10.1016/j.tetlet.2005.07.054

Reference yield: 99.0%

(1R,2R,3S,4R)-2,3,4-tri-O-benzyl-1-O-pivaloyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol (866336-50-7) → (1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol (99695-34-8)

Guidance literature:

With sodium methylate; In methanol; at 40 ℃;

DOI:10.1016/j.tetlet.2005.07.054

upstream raw materials:

(3R,4S,5S,6R)-1,3,4,5-tetra-O-benzyl-6-O-pivaloyl-2-methylene-oct-7-ene-1,3,4,5,6-pentaol

(3R,4S,5S,6R)-1,3,4,5-tetra-O-benzyl-6-O-pivaloyl-1,3,4,5,6-pentahydroxy-oct-7-en-2-one

Downstream raw materials:

(1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol