(3aR,5R,6S,6aR)-6-((2R,3S,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

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-6-((2R,3S,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
• CAS No.: 79384-15-9
• Molecular Formula: C₄₅H₅₂O₁₀Se
• Molecular Weight: 831.862

Synonyms:

Chemical Property of (3aR,5R,6S,6aR)-6-((2R,3S,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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3aR,5R,6S,6aR)-6-((2R,3S,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

There total 6 articles about (3aR,5R,6S,6aR)-6-((2R,3S,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 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:

1,2:5,6-diacetone-D-glucose (582-52-5) + Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester (120316-50-9) → (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 (79384-15-9,79384-16-0) + (3aR,5R,6S,6aR)-6-((2R,3S,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 (79384-15-9,79384-16-0)

Guidance literature:

With 4 A molecular sieve; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at 0 ℃; for 0.25h; Yield given. Yields of byproduct given;

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

Reference yield:

1,2:5,6-diacetone-D-glucose (582-52-5) + Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester (120316-50-9) → (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 (79384-15-9,79384-16-0) + (3aR,5R,6S,6aR)-6-((2R,3S,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 (79384-15-9,79384-16-0)

Guidance literature:

With 4 A molecular sieve; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at 0 ℃; for 0.25h; Yield given. Yields of byproduct given;

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

Reference yield:

Phenylselenyl chloride (5707-04-0) → (3aR,5R,6S,6aR)-6-((2R,3S,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 (79384-15-9,79384-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 1 h / 25 °C

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

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

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

upstream raw materials:

1,2:5,6-diacetone-D-glucose

Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester

Phenylselenyl chloride

3,4,6-tri-O-benzyl-D-glucal

Downstream raw materials:

(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

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