3,5-di-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose

Base Information

• Chemical Name: 3,5-di-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose
• CAS No.: 144402-16-4
• Molecular Formula: C₂₈H₃₀O₅
• Molecular Weight: 446.543
• Mol file: 144402-16-4.mol

Synonyms:3,5-di-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose

Chemical Property of 3,5-di-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-di-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose

There total 11 articles about 3,5-di-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose 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%

benzyl bromide (100-39-0) + 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose (18439-43-5,18439-42-4) → 3,5-di-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose (144402-16-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2006.09.005

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose (20715-20-2) → 3,5-di-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose (144402-16-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / NaBH₄ / methanol / 4 h / 0 - 20 °C

2: 98 percent / NaH; TBAI / tetrahydrofuran / 2 h / 20 °C

With sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1016/j.tet.2006.09.005

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 3,5-di-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose (144402-16-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 7 percent / tetrahydrofuran / 12 h / 20 °C

2: 98 percent / NaH; TBAI / tetrahydrofuran / 2 h / 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1016/j.tet.2006.09.005

upstream raw materials:

benzyl bromide

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose

1,2-O-isopropylidene-5-C-phenyl-β-L-ido/α-D-gluco-pentofuranose

((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-phenyl-methanol

Downstream raw materials:

5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one

(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal

(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate

(E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester