(1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol

Base Information

• Chemical Name: (1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol
• CAS No.: 140849-67-8
• Molecular Formula: C₃₇H₄₀O₆S₂
• Molecular Weight: 644.853

Synonyms:(1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol

Chemical Property of (1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol

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Technology Process of (1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol

There total 1 articles about (1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol 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:

2,3,4,6-Tetra-O-benzyl-1-C--D-xylo-5-hexosulose (140658-51-1) → (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-6,6-bis(methylthio)-1,2,3,4-cyclohexanetetrol (116308-20-4) + (1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol (140849-67-8)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In toluene; for 18h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00039a025

Reference yield: 85.0%

(1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol (140849-67-8) → (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-5-hydroxy-cyclohexanone + (2S,3R,4S,5S,6R)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-3-hydroxy-2-methylsulfanyl-cyclohexanone

Guidance literature:

With ammonium chloride; nickel dichloride; zinc; In tetrahydrofuran; water; at 20 ℃; for 20h;

DOI:10.1021/jo0101003

Reference yield: 65.0%

(1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol (140849-67-8) → (4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone (140658-59-9)

Guidance literature:

nickel; In 1,4-dioxane; at 80 ℃; for 1h;

DOI:10.1021/jo00039a025

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-1-C--D-xylo-5-hexosulose

Downstream raw materials:

(4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone

2,3,4,7-tetra-O-benzyl-5-epi-(6-⁽²⁾H₂)valiolone

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