2-[bis(allyloxy)phosphoryloxy]ethyl 4,6-O-benzylidene-3-O-dodecyl-2-O-{(R)-3-[(4-methoxybenzyl)oxy]tetradecyl}-α-D-glucopyranoside

Base Information

• Chemical Name: 2-[bis(allyloxy)phosphoryloxy]ethyl 4,6-O-benzylidene-3-O-dodecyl-2-O-{(R)-3-[(4-methoxybenzyl)oxy]tetradecyl}-α-D-glucopyranoside
• CAS No.: 855181-56-5
• Molecular Formula: C₅₅H₈₉O₁₂P
• Molecular Weight: 973.278
• Mol file: 855181-56-5.mol

Synonyms:

Chemical Property of 2-[bis(allyloxy)phosphoryloxy]ethyl 4,6-O-benzylidene-3-O-dodecyl-2-O-{(R)-3-[(4-methoxybenzyl)oxy]tetradecyl}-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[bis(allyloxy)phosphoryloxy]ethyl 4,6-O-benzylidene-3-O-dodecyl-2-O-{(R)-3-[(4-methoxybenzyl)oxy]tetradecyl}-α-D-glucopyranoside

There total 8 articles about 2-[bis(allyloxy)phosphoryloxy]ethyl 4,6-O-benzylidene-3-O-dodecyl-2-O-{(R)-3-[(4-methoxybenzyl)oxy]tetradecyl}-α-D-glucopyranoside 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:

Phosphorous acid diallyl ester 2-{(2R,4aR,6S,7R,8S,8aR)-8-dodecyloxy-7-[(R)-3-(4-methoxy-benzyloxy)-tetradecyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy}-ethyl ester → 2-[bis(allyloxy)phosphoryloxy]ethyl 4,6-O-benzylidene-3-O-dodecyl-2-O-{(R)-3-[(4-methoxybenzyl)oxy]tetradecyl}-α-D-glucopyranoside (855181-56-5)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2005.03.034

Reference yield:

(R)-1-methanesulfonyloxy-3-(4-methoxybenzyloxy)tetradecane (288402-98-2) → 2-[bis(allyloxy)phosphoryloxy]ethyl 4,6-O-benzylidene-3-O-dodecyl-2-O-{(R)-3-[(4-methoxybenzyl)oxy]tetradecyl}-α-D-glucopyranoside (855181-56-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 67 percent / sodium hydride / dimethylformamide / 6 h / 20 °C

2: OsO₄; sodium periodate / acetone; H₂O / 4 h / 20 °C

3: 1.05 g / NaBH₄ / ethanol / 1 h / 20 °C

4: 1H-tetrazole / tetrahydrofuran / 4 h / 20 °C

5: 1.07 g / H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

With 1H-tetrazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; dihydrogen peroxide; sodium hydride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tet.2005.03.034

Reference yield:

allyl 3-O-dodecyl-α-D-glucopyranoside (637354-71-3) → 2-[bis(allyloxy)phosphoryloxy]ethyl 4,6-O-benzylidene-3-O-dodecyl-2-O-{(R)-3-[(4-methoxybenzyl)oxy]tetradecyl}-α-D-glucopyranoside (855181-56-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / 4-methylbenzenesulfonic acid monohydrate / dimethylformamide / 16 h / 20 °C

2: 67 percent / sodium hydride / dimethylformamide / 6 h / 20 °C

3: OsO₄; sodium periodate / acetone; H₂O / 4 h / 20 °C

4: 1.05 g / NaBH₄ / ethanol / 1 h / 20 °C

5: 1H-tetrazole / tetrahydrofuran / 4 h / 20 °C

6: 1.07 g / H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

With 1H-tetrazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; p-toluenesulfonic acid monohydrate; dihydrogen peroxide; sodium hydride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tet.2005.03.034

upstream raw materials:

(R)-1-methanesulfonyloxy-3-(4-methoxybenzyloxy)tetradecane

allyl 3-O-dodecyl-α-D-glucopyranoside

allyl 4,6-O-benzylidene-3-O-dodecyl-α-D-glucopyranoside

allyl 4,6-O-benzylidene-3-O-dodecyl-2-O-{(R)-3-[(4-methoxybenzyl)oxy]tetradecyl}-α-D-glucopyranoside

Downstream raw materials:

2-[bis(allyloxy)phosphoryloxy]ethyl 4,6-O-benzylidene-3-O-dodecyl-2-O-[3-oxotetradecyl]-α-D-glucopyranoside