6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose

Base Information

• Chemical Name: 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose
• CAS No.: 114475-11-5
• Molecular Formula: C₂₁H₂₆O₆
• Molecular Weight: 374.434
• Mol file: 114475-11-5.mol

Synonyms:6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose

Chemical Property of 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose

There total 1 articles about 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose 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: 79.7%

7,8-dideoxy-1,2:3,4-di-O-isopropylidene-6(S)-hydroxy-α-D-galacto-oct-7-inopyranose (4977-08-6) + benzyl bromide (100-39-0) → 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose (114475-11-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/0008-6215(87)80058-7

Reference yield:

6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose (114475-11-5) → 3-O-benzyl-6-C-<(E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-heptopyranos-7-ylidene>-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (114475-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tributyltin hydride, azobis(isobutyronitrile); 2.) butyl-lithium / 1.) xylene, reflux, 3 h; 2.) tetrahydrofuran-hexane, -78 deg C, 1 h

2: tetrahydrofuran; hexane / 2 h / -78 °C

3: 77.5 percent / Jones reagent / acetone

With n-butyllithium; jones reagent; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; hexane; acetone;

DOI:10.1016/0008-6215(87)80058-7

Reference yield:

6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-oct-7-ynopyranose (114475-11-5) → 3-O-benzyl-6-C-<(E)-6-O-benzyl-7-deoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranos-7-ylidene>-6-deoxy-1,2-O-isopropyledene-α-D-glucofuranose (114475-14-8,114530-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) tributyltin hydride, azobis(isobutyronitrile); 2.) butyl-lithium / 1.) xylene, reflux, 3 h; 2.) tetrahydrofuran-hexane, -78 deg C, 1 h

2: tetrahydrofuran; hexane / 2 h / -78 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; hexane;

DOI:10.1016/0008-6215(87)80058-7

upstream raw materials:

7,8-dideoxy-1,2:3,4-di-O-isopropylidene-6(S)-hydroxy-α-D-galacto-oct-7-inopyranose

benzyl bromide

Downstream raw materials:

3-O-benzyl-6-C-<(E)-6-O-benzyl-7-deoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranos-7-ylidene>-6-deoxy-1,2-O-isopropyledene-α-D-glucofuranose

3-O-benzyl-6-C-<(E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-heptopyranos-7-ylidene>-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose

3-O-benzyl-6-C-<(E)-6-O-benzyl-7-deoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galacto-heptopyranos-7-ylidene>-6-deoxy-1,2-O-isopropylidene-α-D-gluco-furanose