(2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran
• CAS No.: 84207-63-6
• Molecular Formula: C₃₃H₄₀O₇
• Molecular Weight: 548.676

Synonyms:(2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran

Chemical Property of (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran

Chemical Property:

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Technology Process of (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran

There total 2 articles about (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran 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: 75.0%

(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-iodo-tetrahydro-pyran (84207-60-3) → (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran (84207-63-6)

Guidance literature:

With lithium aluminium tetrahydride; triphenyltin chloride; for 12h; Ambient temperature;

DOI:10.1246/cl.1982.1525

Reference yield:

(Z)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-hex-5-en-2-ol (84207-55-6,112419-97-3) → (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran (84207-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / N-iodosuccinimide / various solvent(s) / 3 h / -78 °C

2: 75 percent / LiAlH₄ / Ph₃SnCl / 12 h / Ambient temperature

With N-iodo-succinimide; lithium aluminium tetrahydride; triphenyltin chloride; In various solvent(s);

DOI:10.1246/cl.1982.1525

Reference yield: 85.0%

(2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran (84207-63-6) → (R)-3-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propane-1,2-diol (84207-64-7)

Guidance literature:

With acetic acid; In chloroform; for 16h; Ambient temperature;

DOI:10.1246/cl.1982.1525

upstream raw materials:

(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-iodo-tetrahydro-pyran

(Z)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-hex-5-en-2-ol

Downstream raw materials:

(R)-3-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propane-1,2-diol

Hexadecanoic acid (S)-2-((2S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-1-hexadecanoyloxymethyl-ethyl ester

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