(2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one

Base Information

• Chemical Name: (2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one
• CAS No.: 345342-55-4
• Molecular Formula: C₂₆H₃₀O₆
• Molecular Weight: 438.521
• Mol file: 345342-55-4.mol

Synonyms:(2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one

Chemical Property of (2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one

There total 2 articles about (2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one 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: 100.0%

(2R,3R,4S,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-ol (345342-61-2) → (2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one (345342-55-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 1h;

DOI:10.1021/ol010089t

Reference yield:

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside (79549-73-8) → (2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one (345342-55-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / sodium hydride / dimethylformamide / 0.5 h / 20 °C

2: 93 percent / sodium cyanoborohydride; HCl; 3 Angstroem molecular sieve / tetrahydrofuran; diethyl ether / 0.17 h

3: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

With hydrogenchloride; 3 A molecular sieve; sodium hydride; sodium cyanoborohydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol010089t

Reference yield: 66.0%

methyllithium (917-54-4) + (2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one (345342-55-4) → (2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol (345342-56-5) + (2R,3S,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol

Guidance literature:

In diethyl ether;

DOI:10.1016/S0040-4039(01)00355-0

upstream raw materials:

(2R,3R,4S,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-ol

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside

Downstream raw materials:

(2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol

(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

nafuredin

Benzoic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-5-methyl-tetrahydro-pyran-3-yl ester