Pent-4-enyl 2,2',3,3',6,6'-hexa-O-benzyl-β-D-lactoside

Base Information

• Chemical Name: Pent-4-enyl 2,2',3,3',6,6'-hexa-O-benzyl-β-D-lactoside
• CAS No.: 284663-04-3
• Molecular Formula: C₅₉H₆₆O₁₁
• Molecular Weight: 951.166
• Mol file: 284663-04-3.mol

Synonyms:Pent-4-enyl 2,2',3,3',6,6'-hexa-O-benzyl-β-D-lactoside

Chemical Property of Pent-4-enyl 2,2',3,3',6,6'-hexa-O-benzyl-β-D-lactoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pent-4-enyl 2,2',3,3',6,6'-hexa-O-benzyl-β-D-lactoside

There total 7 articles about Pent-4-enyl 2,2',3,3',6,6'-hexa-O-benzyl-β-D-lactoside 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: 79.0%

(2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (284663-21-4) → Pent-4-enyl 2,2',3,3',6,6'-hexa-O-benzyl-β-D-lactoside (284663-04-3)

Guidance literature:

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.166667h;

DOI:10.1002/(SICI)1521-3765(20000417)6:8<1366::AID-CHEM1366>3.0.CO;2-K

Reference yield:

n-pentenyl (β-D-galactopyranosyl)-(1<*>4)-β-D-glucopyranoside (153228-87-6) → Pent-4-enyl 2,2',3,3',6,6'-hexa-O-benzyl-β-D-lactoside (284663-04-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Bu₂SnO / benzene / 15 h / Heating

1.2: 54 percent / Bu₄NI / benzene / 3.5 h / Heating

2.1: 72 percent / CSA / acetonitrile; dimethylformamide / 16 h / 20 °C

3.1: 97 percent / Et₄NI; NaH / dimethylformamide / 14 h / 0 - 20 °C

4.1: 79 percent / NaCNBH₃; molecular sieves 4 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.17 h / 20 °C

With hydrogenchloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetraethylammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Cyclization / 1.2: Etherification / 2.1: Cyclization / 3.1: Etherification / 4.1: Ring cleavage;

DOI:10.1002/(SICI)1521-3765(20000417)6:8<1366::AID-CHEM1366>3.0.CO;2-K

Reference yield:

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-60-8,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4) → Pent-4-enyl 2,2',3,3',6,6'-hexa-O-benzyl-β-D-lactoside (284663-04-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 96 percent / HBr; Ac₂O / acetic acid / 3 h / 0 - 20 °C

2.1: 75 percent / Ag₂CO₃; molecular sieves 4 Angstroem; I₂ / CH₂Cl₂ / 16 h / 20 °C

3.1: 100 percent / NaOMe / methanol / 16 h / 20 °C

4.1: Bu₂SnO / benzene / 15 h / Heating

4.2: 54 percent / Bu₄NI / benzene / 3.5 h / Heating

5.1: 72 percent / CSA / acetonitrile; dimethylformamide / 16 h / 20 °C

6.1: 97 percent / Et₄NI; NaH / dimethylformamide / 14 h / 0 - 20 °C

7.1: 79 percent / NaCNBH₃; molecular sieves 4 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.17 h / 20 °C

With hydrogenchloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetraethylammonium iodide; hydrogen bromide; iodine; sodium methylate; acetic anhydride; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; silver carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Substitution / 2.1: Glycosidation / 3.1: Deacetylation / 4.1: Cyclization / 4.2: Etherification / 5.1: Cyclization / 6.1: Etherification / 7.1: Ring cleavage;

DOI:10.1002/(SICI)1521-3765(20000417)6:8<1366::AID-CHEM1366>3.0.CO;2-K

upstream raw materials:

(2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

n-pentenyl (β-D-galactopyranosyl)-(1<*>4)-β-D-glucopyranoside

2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose

Downstream raw materials:

C₉₄H₁₀₂O₁₇

C₉₃H₁₀₀O₁₆