(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside

Base Information

• Chemical Name: (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside
• CAS No.: 79384-23-9
• Molecular Formula: C₃₉H₄₈O₁₀
• Molecular Weight: 676.804
• Mol file: 79384-23-9.mol

Synonyms:(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside

Chemical Property of (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside

There total 16 articles about (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside 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: 78.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9) + (2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran (128573-17-1) → (3aR,5R,6aR)-6-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (79384-20-6,79384-23-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane;

DOI:10.1039/c39900000270

Reference yield: 46.0%

p-toulenesulfonyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside (79384-23-9)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 - 20 ℃; for 18.25h; stereoselective reaction;

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → (3aR,5R,6S,6aR)-6-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (79384-20-6,79384-23-9)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 1 h / 25 °C

2: molecular sieves 4A / TMSOTf / diethyl ether / 0.25 h / 0 °C

3: Ph₃SnH / toluene / Heating

With 4 A molecular sieve; triphenylstannane; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; toluene;

DOI:10.1016/S0040-4039(01)80327-0

upstream raw materials:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

(2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran

(3aR,5R,6S,6aR)-6-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Dithiocarbonic acid O-{(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-3-yl} ester S-methyl ester