(1S,2S)-2-hydroxycyclohexyl α-D-glucopyranoside

Base Information

• Chemical Name: (1S,2S)-2-hydroxycyclohexyl α-D-glucopyranoside
• CAS No.: 76035-73-9
• Molecular Formula: C₁₂H₂₂O₇
• Molecular Weight: 278.302
• Mol file: 76035-73-9.mol

Synonyms:(1S,2S)-2-hydroxycyclohexyl α-D-glucopyranoside

Chemical Property of (1S,2S)-2-hydroxycyclohexyl α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-2-hydroxycyclohexyl α-D-glucopyranoside

There total 8 articles about (1S,2S)-2-hydroxycyclohexyl α-D-glucopyranoside 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: 71.0%

(1S,2S)-2-hydroxycyclohexyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (122992-43-2) → (1R,2R)-2-hydroxycyclohexyl α-D-glucopyranoside (69485-30-9) + (1S,2S)-2-hydroxycyclohexyl α-D-glucopyranoside (76035-73-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetic acid; for 16h; under 750.06 Torr;

Reference yield:

trans-1,2-cyclohexandiol (1460-57-7) → (1S,2S)-2-hydroxycyclohexyl α-D-glucopyranoside (76035-73-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Hepes buffer; Catharanthus roseus GTF-I glucosyltransferase / 24 h / 35 °C / pH 7.0 / Enzymatic reaction

2: 1,1,3,3-tetramethylguanidine; BF₃*OEt₂ / acetonitrile / 2 h / 20 °C

3: K₂CO₃ / H₂O

With HEPES buffer; boron trifluoride diethyl etherate; potassium carbonate; N,N,N',N'-tetramethylguanidine; Catharanthus roseus GTF-I glucosyltransferase; In water; acetonitrile;

DOI:10.1016/j.tetasy.2004.06.022

Reference yield:

1,2-Cyclohexanediol (931-17-9) + phenyl-β-D-galactopyranoside (2818-58-8) → (2R,3R,4S,5R,6R)-2-((1R,2S)-2-Hydroxy-cyclohexyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (69485-30-9,69501-34-4,69501-35-5,69501-36-6,69501-37-7,69501-38-8,76035-73-9,120328-84-9,120328-85-0,147202-32-2) + (2R,3R,4S,5R,6R)-2-((1S,2R)-2-Hydroxy-cyclohexyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (69485-30-9,69501-34-4,69501-35-5,69501-36-6,69501-37-7,69501-38-8,76035-73-9,120328-84-9,120328-85-0,147202-32-2)

Guidance literature:

ECβG enzyme; In water; at 0 - 23 ℃; Yields of byproduct given. Title compound not separated from byproducts; pH= 7.3; Var. cat.: AOβG, var. solv. and pH; d.e.= 90percent;

DOI:10.1016/S0040-4039(00)82178-4

upstream raw materials:

1,2-Cyclohexanediol

phenyl-β-D-galactopyranoside

(1S,2S)-2-hydroxycyclohexyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

trans-1,2-cyclohexandiol

Downstream raw materials:

(1S,2S)-trans-1,2-Cyclohexanediol

Refernces

• 1、 Bock, Klaus,Refn, Susanne. "The Substrate Specificity of Amyloglucosidase (AMG). Part IV. Hydroxycyclohexyl Glucosides". . p. 373 - 380. Retrieved 2007/10/02.