(1R,2R) 2-hydroxy-cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside

Base Information

• Chemical Name: (1R,2R) 2-hydroxy-cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside
• CAS No.: 293752-49-5
• Molecular Formula: C₄₀H₃₈O₁₁
• Molecular Weight: 694.735
• Mol file: 293752-49-5.mol

Synonyms:(1R,2R) 2-hydroxy-cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside

Chemical Property of (1R,2R) 2-hydroxy-cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R) 2-hydroxy-cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside

There total 1 articles about (1R,2R) 2-hydroxy-cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside 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: 73.0%

(1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) + 2,3,4,6-tetra-O-benzoyl-α,b-D-galactopyranosyl trichloroacetimidate (203435-09-0) → (1R,2R) 2-hydroxy-cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside (293752-49-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1139/v00-081

Reference yield: 75.0%

(1R,2R) 2-hydroxy-cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside (293752-49-5) → (1R,2R) 2-hydroxy-cyclohexyl β-D-galactopyranoside (294677-28-4)

Guidance literature:

With methanol; sodium methylate; for 6h;

DOI:10.1139/v00-081

Reference yield:

(1R,2R) 2-hydroxy-cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside (293752-49-5) → 2-O-{1-O-[(1R,2R) 2-O-(α-L-fucopyranosyl)cyclohexyl]β-D-galactopyranos-3-yl} 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / MeONa; MeOH / 6 h

2: 64 percent / α(2-3)sialyl transferase; calf intestine alkaline phosphatase; further reagents / H2O / 29 h / 37 °C

3: 71 percent / FucT III; calf intestine alkaline phosphatase; further reagents / H₂O / 24 h / 37 °C

With methanol; α(2-3)sialyl transferase; calf intestine alkaline phosphatase; FucT III; sodium methylate; In water; 1: debenzoylation / 2: glycosylation / 3: glycosylation;

DOI:10.1139/v00-081

upstream raw materials:

(1R,2R)-trans-1,2-cyclohexanediol

2,3,4,6-tetra-O-benzoyl-α,b-D-galactopyranosyl trichloroacetimidate

Downstream raw materials:

(1R,2R) 2-hydroxy-cyclohexyl β-D-galactopyranoside

(1R,2R) 2-hydroxy-cyclohexyl 3-O-[2-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosonate)]-β-D-galactopyranoside

Refernces