(3R,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Base Information

• Chemical Name: (3R,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
• CAS No.: 65620-65-7
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.307
• Mol file: 65620-65-7.mol

Synonyms:(3R,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Chemical Property of (3R,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

There total 16 articles about (3R,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 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: 95.0%

α-D-glucopyranose peracetylate (604-68-2) → 1,2,3,4-tetra-O-acetyl-α-D-glucopyranoside (13100-46-4,18977-22-5,27539-65-7,28154-37-2,51008-88-9,51897-82-6,57128-41-3,61474-17-7,65620-65-7,70613-80-8,73366-80-0,78148-86-4,80184-00-5,104195-07-5)

Guidance literature:

With Candida rugosa lipase on Lewatit₁₆₀₀; In aq. phosphate buffer; acetonitrile; at 25 ℃; pH=4.8; Reagent/catalyst; Enzymatic reaction;

DOI:10.1002/cctc.201601632

Reference yield: 80.0%

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 1,2,3,4-tetra-O-acetyl-α-D-glucopyranoside (13100-46-4,18977-22-5,27539-65-7,28154-37-2,51008-88-9,51897-82-6,57128-41-3,61474-17-7,65620-65-7,70613-80-8,73366-80-0,78148-86-4,80184-00-5,104195-07-5)

Guidance literature:

With sodium acetate; In water; acetonitrile; for 24h; pH=5; regioselective reaction; Enzymatic reaction;

DOI:10.1016/j.molcatb.2014.05.008

Reference yield: 73.0%

α-D-glucopyranose peracetylate (604-68-2) → 1,2,3-tri-O-acetyl-α-D-glucopyranose (116559-76-3) + 1,2,3,4-tetra-O-acetyl-α-D-glucopyranoside (13100-46-4,18977-22-5,27539-65-7,28154-37-2,51008-88-9,51897-82-6,57128-41-3,61474-17-7,65620-65-7,70613-80-8,73366-80-0,78148-86-4,80184-00-5,104195-07-5)

Guidance literature:

In N,N-dimethyl-formamide; for 36h; candida cylindracea lipase (CCL); pH 7;

DOI:10.1021/jo00256a008

upstream raw materials:

1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-glucopyranose

α-D-glucopyranose peracetylate

D-glucose pentaacetate

1,2,3,4-tetra-O-acetyl-6-O-benzoyl-α-D-glucopyranose

Downstream raw materials:

1,2,3,4-tetra-O-acetyl-6-O-benzoyl-α-D-glucopyranose

(1S,2S,3R)-5-Oxo-N-phenyl-3-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyloxy)cyclohexane-1,2-dicarboximide

(1S,2S,3R)-5-oxo-N-phenyl-3-(2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)cyclohexane-1,2-dicarboximide

(1S,2S,3R)-5-(t-butyldimethylsiloxy)-N-phenyl-3-<2',3',4'-tri-O-acetyl-6'-O-(t-butyldimethylsilyl)-α-D-glucopyranosyloxy>cyclohex-4-ene-1,2-dicarboximide

Refernces

• 1、 Jiang, Xuefeng,Li, Jiagen,Wang, Ming. "Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement". supporting information. p. 9053 - 9057. Retrieved 2021/11/30.
• 2、 Callaghan, Ciara,Redmond, Martin,Alnoch, Robson Carlos,Mateo, Cesar,Filice, Marco,Palomo, Jose M.. "Biocatalytic Process Optimization for the Production of High-Added-Value 6-O-Hydroxy and 3-O-Hydroxy Glycosyl Building Blocks". . p. 2536 - 2543. Retrieved 2017/07/13.