2,6:7,11-dianhydro-5,8-dideoxy-1,3,4,9,10,12-hexakis-O-benzyl-D-erythro-L-gulo-dodeco-5,7-dienitol

Base Information

• Chemical Name: 2,6:7,11-dianhydro-5,8-dideoxy-1,3,4,9,10,12-hexakis-O-benzyl-D-erythro-L-gulo-dodeco-5,7-dienitol
• CAS No.: 142270-14-2
• Molecular Formula: C₅₄H₅₄O₈
• Molecular Weight: 831.018
• Mol file: 142270-14-2.mol

Synonyms:2,6:7,11-dianhydro-5,8-dideoxy-1,3,4,9,10,12-hexakis-O-benzyl-D-erythro-L-gulo-dodeco-5,7-dienitol

Chemical Property of 2,6:7,11-dianhydro-5,8-dideoxy-1,3,4,9,10,12-hexakis-O-benzyl-D-erythro-L-gulo-dodeco-5,7-dienitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6:7,11-dianhydro-5,8-dideoxy-1,3,4,9,10,12-hexakis-O-benzyl-D-erythro-L-gulo-dodeco-5,7-dienitol

There total 3 articles about 2,6:7,11-dianhydro-5,8-dideoxy-1,3,4,9,10,12-hexakis-O-benzyl-D-erythro-L-gulo-dodeco-5,7-dienitol 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: 90.0%

3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-D-glucal (105938-01-0) → 2,6:7,11-dianhydro-5,8-dideoxy-1,3,4,9,10,12-hexakis-O-benzyl-D-erythro-L-gulo-dodeco-5,7-dienitol (142270-14-2)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); copper(I) thiophene-2-carboxylate; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1080/07328303.2018.1508590

Reference yield: 52.0%

Vinyl bromide (593-60-2,25951-54-6) + 3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-D-glucal (105938-01-0) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-vinyl-D-arabino-hex-1-enitol (130912-32-2) + 2,6:7,11-dianhydro-5,8-dideoxy-1,3,4,9,10,12-hexakis-O-benzyl-D-erythro-L-gulo-dodeco-5,7-dienitol (142270-14-2)

Guidance literature:

dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90552-4

Reference yield:

1,5-anhydro-3,4,6-tri-O-phenylmethyl-1,2-dideoxy-1-[(Ss)-phenylsulfinyl]-D-arabino-hex-1-enitol → 2,6:7,11-dianhydro-5,8-dideoxy-1,3,4,9,10,12-hexakis-O-benzyl-D-erythro-L-gulo-dodeco-5,7-dienitol (142270-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: phenyllithium / Inert atmosphere

1.2: -78 °C / Inert atmosphere

2.1: dichloro bis(acetonitrile) palladium(II); copper(I) thiophene-2-carboxylate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere

With dichloro bis(acetonitrile) palladium(II); copper(I) thiophene-2-carboxylate; phenyllithium; In N,N-dimethyl-formamide; 2.1: |Stille Cross Coupling;

DOI:10.1080/07328303.2018.1508590

upstream raw materials:

Vinyl bromide

3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-D-glucal

Downstream raw materials:

2,6:7,11-dianhydro-1,3,4,9,10,12-hexa-O-benzyl-D-erythro-L-galacto-L-gulo-dodecitol

(2R,3R,4R,5R,6R,2'S,3'R,4'R,5'R,6'R)-4,5,4',5'-Tetrakis-benzyloxy-6,6'-bis-benzyloxymethyl-octahydro-[2,2']bipyranyl-3,3'-diol