3-O-benzyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylofuranose

Base Information

• Chemical Name: 3-O-benzyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylofuranose
• CAS No.: 97782-09-7
• Molecular Formula: C₁₉H₂₉O₇P
• Molecular Weight: 400.409
• Mol file: 97782-09-7.mol

Synonyms:3-O-benzyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylofuranose

Chemical Property of 3-O-benzyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylofuranose

There total 1 articles about 3-O-benzyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylofuranose 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: 82.0%

(3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (29580-99-2) + triethyl phosphite (122-52-1) → 3-O-benzyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylofuranose (97782-09-7)

Guidance literature:

at 150 ℃; for 15h;

DOI:10.1021/jo00219a018

Reference yield:

3-O-benzyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylofuranose (97782-09-7) → 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-C-phosphino-α-D-xylofuranose (97782-10-0)

Guidance literature:

With dihydrobis(2-methoxyethyl)aluminate; In toluene; benzene; at 5 ℃; for 1h;

DOI:10.1021/jo00219a018

Reference yield:

3-O-benzyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylofuranose (97782-09-7) → 3-O-benzyl-5-deoxy-5-C-phosphinyl-D-xylopyranose (97782-12-2)

Guidance literature:

Multi-step reaction with 3 steps

1: dihydrobis(2-methoxyethyl)aluminate (SDMA) / benzene; toluene / 1 h / 5 °C

2: 2percent aq. H₂O₂ / propan-2-ol

3: 0.5 M aq. HCl / propan-2-ol / 1 h / 100 °C

With hydrogenchloride; dihydrobis(2-methoxyethyl)aluminate; dihydrogen peroxide; In isopropyl alcohol; toluene; benzene;

DOI:10.1021/jo00219a018

upstream raw materials:

(3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

triethyl phosphite

Downstream raw materials:

3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-C-phosphino-α-D-xylofuranose

3-O-benzyl-5-deoxy-5-C-phosphinyl-D-xylopyranose

3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-C-phosphinyl-α-D-xylofuranose

3-O-benzyl-5-deoxy-5-C-(hydroxyphosphinyl)-D-xylopyranose