(1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate

Base Information

• Chemical Name: (1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate
• CAS No.: 220152-90-9
• Molecular Formula: C₂₉H₃₀O₇
• Molecular Weight: 490.553
• Mol file: 220152-90-9.mol

Synonyms:(1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate

Chemical Property of (1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate

There total 6 articles about (1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate 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:

methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside (4356-80-3,34212-64-1,40653-32-5,53008-65-4,68027-27-0,73111-53-2,128184-63-4,138794-99-7,55094-38-7,641635-63-4) → (1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate (220152-90-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-dicyclohexylcarbodiimide; trifluoroacetic acid; pyridine / dimethylsulfoxide; benzene / 24 h / 20 °C

2: Et₃N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating

3: PdCl₂ / dioxane; H₂O / 3 h / 60 °C

With pyridine; dmap; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dichloride; In 1,4-dioxane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; benzene; 3: Ferrier-II rearrangement;

DOI:10.1021/jo001575h

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside (134680-55-0) → (1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate (220152-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating

2: PdCl₂ / dioxane; H₂O / 3 h / 60 °C

With dmap; triethylamine; palladium dichloride; In 1,4-dioxane; water; 1,2-dichloro-ethane; 2: Ferrier-II rearrangement;

DOI:10.1021/jo001575h

Reference yield:

Acetic acid (3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-(2E)-ylidenemethyl ester → (1S,2S,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate (220152-90-9) + (1R,2R,3S,4R,5R)-3,4,5-tri(benzyloxy)-2-hydroxy-6-oxocyclohexyl acetate (220152-88-5)

Guidance literature:

With water; mercury(II) trifluoroacetate; In 1,4-dioxane; at 60 ℃; for 3h; Yield given; Yields of byproduct given;

DOI:10.1016/S0040-4039(98)02231-X

upstream raw materials:

(E)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galacto-hex-5-enopyranoside

(Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galacto-hex-5-enopyranoside

methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside

methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside

Downstream raw materials:

muco-inositol

epi-Inositol

D-2-O-acetyl-4,5,6-tri-O-benzyl-muco-inositol

D-2-O-acetyl-tri-4,5,6-O-benzyl-epi-inositol