2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate

Base Information

• Chemical Name: 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate
• CAS No.: 316172-35-7
• Molecular Formula: C₂₇H₂₈O₆
• Molecular Weight: 448.516
• Mol file: 316172-35-7.mol

Synonyms:2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate

Chemical Property of 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate

There total 8 articles about 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate 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%

methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside (85716-44-5) → 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate (316172-35-7)

Guidance literature:

With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; In water; acetonitrile; at 0 ℃;

DOI:10.1021/ol006714w

Reference yield:

methyl 6-deoxy-α-D-xylo-hex-5-enopyranoside (13265-83-3) → 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate (316172-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide; various solvent(s) / 0 °C

1.2: 68 percent / dimethylformamide; various solvent(s) / 2 h

2.1: 95 percent / oxone; 1,1,1-trifluoroacetone; Na₂EDTA / aq. NaHCO₃ / acetonitrile / 12 h / 0 °C

With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydride; sodium hydrogencarbonate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo016378c

Reference yield:

methyl 2,3,4-tri-O-trimethylsilyl-6-deoxy-6-iodo-α-D-glucopyranoside (59578-04-0) → 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate (316172-35-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DBU / dimethylformamide / 3 h / 75 °C

1.2: 61 percent / pyridine

2.1: 100 percent / NaOMe / methanol / 20 °C

3.1: NaH / dimethylformamide; various solvent(s) / 0 °C

3.2: 68 percent / dimethylformamide; various solvent(s) / 2 h

4.1: 95 percent / oxone; 1,1,1-trifluoroacetone; Na₂EDTA / aq. NaHCO₃ / acetonitrile / 12 h / 0 °C

With Oxone; 1,1,1-trifluoro-2-propanone; sodium methylate; edetate disodium; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydrogencarbonate; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo016378c

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside

(3S,5S,6R,7R,8S)-6,7,8-Tris-benzyloxy-5-methoxy-1,4-dioxa-spiro[2.5]octane

methyl 6-deoxy-α-D-xylo-hex-5-enopyranoside

methyl 2,3,4-tri-O-trimethylsilyl-6-deoxy-6-iodo-α-D-glucopyranoside

Downstream raw materials:

1-O-(2-bromobenzoyl)-2,3,4-tri-O-benzyl-β-D-xylohexoseptanosid-5-ulose

2,3,4-tri-O-benzyl-5-O-tert-butyldimethylsilyl-1,6-anhydro-β-L-idopyranos-5-ulose

2,3,4-tri-O-benzyl-5-O-methyl-1,6-anhydro-β-L-idopyranos-5-ulose

Refernces

• 1、 Skelton, Brian W.,Stick, Robert V.,Stubbs, Keith A.,Watts, Andrew G.,White, Allan H.. "The fluorination (at C5) of some derivatives of D-glucose". . p. 345 - 353. Retrieved 2007/10/03.