1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

Base Information

• Chemical Name: 1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose
• CAS No.: 128442-04-6
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.376
• Mol file: 128442-04-6.mol

Synonyms:1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

Chemical Property of 1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

There total 17 articles about 1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose 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: 98.0%

S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (87470-70-0) → 1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol (110522-37-7,124579-04-0,128442-04-6,124579-02-8)

Guidance literature:

With naphthalen-1-yl-lithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4039(01)80444-5

Reference yield: 98.0%

(2R,6S,7R,8S,8aS)-7,8-bis(benzyloxy)-2-phenyl-6-(phenylthio)hexahydropyrano[3,2-d][1,3]dioxine (496019-46-6) → 1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol (110522-37-7,124579-04-0,128442-04-6,124579-02-8)

Guidance literature:

With naphthalen-1-yl-lithium; In tetrahydrofuran; at -78 - 25 ℃; for 0.25h;

DOI:10.1016/0008-6215(89)84061-3

Reference yield: 85.0%

(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)trimethylsilane (128848-53-3) → 1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol (110522-37-7,124579-04-0,128442-04-6,124579-02-8)

Guidance literature:

With potassium hydride; In tetrahydrofuran; for 0.333333h; Ambient temperature;

DOI:10.1016/S0040-4020(01)97585-4

upstream raw materials:

(3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)trimethylsilane

phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside

S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

(2R,6S,7R,8S,8aS)-7,8-bis(benzyloxy)-2-phenyl-6-(phenylthio)hexahydropyrano[3,2-d][1,3]dioxine

Downstream raw materials:

(2R,3R,4S,5S,6S)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran-3-ol

(2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran-3-ol

(2R,4aR,6S,7S,8S,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine

(2R,4aR,6R,7R,8S,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine