(3aS,4aR,7aR,7bR)-2-Ethyl-6,6-dimethyl-3-trityloxymethyl-tetrahydro-[1,3]dioxolo[4',5':4,5]furo[2,3-d][1,2]oxaphosphole 2-oxide

Base Information

• Chemical Name: (3aS,4aR,7aR,7bR)-2-Ethyl-6,6-dimethyl-3-trityloxymethyl-tetrahydro-[1,3]dioxolo[4',5':4,5]furo[2,3-d][1,2]oxaphosphole 2-oxide
• CAS No.: 84175-69-9
• Molecular Formula: C₃₀H₃₃O₆P
• Molecular Weight: 520.562
• Mol file: 84175-69-9.mol

Synonyms:

Chemical Property of (3aS,4aR,7aR,7bR)-2-Ethyl-6,6-dimethyl-3-trityloxymethyl-tetrahydro-[1,3]dioxolo[4',5':4,5]furo[2,3-d][1,2]oxaphosphole 2-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4aR,7aR,7bR)-2-Ethyl-6,6-dimethyl-3-trityloxymethyl-tetrahydro-[1,3]dioxolo[4',5':4,5]furo[2,3-d][1,2]oxaphosphole 2-oxide

There total 6 articles about (3aS,4aR,7aR,7bR)-2-Ethyl-6,6-dimethyl-3-trityloxymethyl-tetrahydro-[1,3]dioxolo[4',5':4,5]furo[2,3-d][1,2]oxaphosphole 2-oxide 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:

3,6-Di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose(E,Z)-5-(p-tolylsulfonyl)hydrazone (81823-13-4,81823-14-5) → (5S)-5-Deoxy-5-C-<(S)-O-cyclo-ethylphosphinyl>-1,2-O-isopropylidene-6-O-(triphenylmethyl)-α-D-xylo-hexofuranose (84175-69-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / benzene / 35 h / 20 °C

2: 66 percent / 1.) NaBH₄, 2.) acetic acid / tetrahydrofuran / 1.) 20 deg C, 23 h, 2.) 0 deg C, pH 4

3: H₂ / Pd/C / ethanol / 40 °C

4: pyridine / 84 h / 35 - 40 °C

With sodium tetrahydroborate; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; benzene;

DOI:10.1021/jo00152a006

Reference yield:

(5RS)-3,6-Di-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-C-(ethylmethoxyphosphinyl)-5-C-<(p-tolylsulfonyl)-hydrazino>-α-D-xylo-hexofuranose (84175-56-4,84175-57-5,84175-58-6,84175-59-7) → (5S)-5-Deoxy-5-C-<(S)-O-cyclo-ethylphosphinyl>-1,2-O-isopropylidene-6-O-(triphenylmethyl)-α-D-xylo-hexofuranose (84175-69-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / 1.) NaBH₄, 2.) acetic acid / tetrahydrofuran / 1.) 20 deg C, 23 h, 2.) 0 deg C, pH 4

2: H₂ / Pd/C / ethanol / 40 °C

3: pyridine / 84 h / 35 - 40 °C

With sodium tetrahydroborate; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol;

DOI:10.1021/jo00152a006

Reference yield:

trityl chloride (76-83-5) + (5RS)-5-Deoxy-5-C-<(RS)-3-O-cyclo-ethylphosphinyl>-1,2-O-isopropylidene-α-D-xylo-hexofuranose (84175-64-4,84175-65-5,84175-66-6,84175-67-7) → (5R)-5-Deoxy-5-C-<(R)-O-cyclo-ethylphosphinyl>-1,2-O-isopropylidene-6-O-(triphenylmethyl)-α-D-xylo-hexofuranose (84175-68-8) + (5S)-5-Deoxy-5-C-<(S)-O-cyclo-ethylphosphinyl>-1,2-O-isopropylidene-6-O-(triphenylmethyl)-α-D-xylo-hexofuranose (84175-69-9)

Guidance literature:

In pyridine; at 35 - 40 ℃; for 84h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00152a006

upstream raw materials:

trityl chloride

(5RS)-5-Deoxy-5-C-<(RS)-3-O-cyclo-ethylphosphinyl>-1,2-O-isopropylidene-α-D-xylo-hexofuranose

3,6-Di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose(E,Z)-5-(p-tolylsulfonyl)hydrazone

(5RS)-3,6-Di-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-C-(ethylmethoxyphosphinyl)-5-C-<(p-tolylsulfonyl)-hydrazino>-α-D-xylo-hexofuranose

Downstream raw materials:

(5RS)-5-Deoxy-5-C-<(RS)-ethylphosphinyl>-1,2-O-isopropylidene-6-O-(triphenylmethyl)-α-D-xylo-hexofuranose