(2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol
CAS No.:219864-84-3
Molecular Formula:C₂₀H₂₄O₆
Molecular Weight:360.407
Hs Code.:

Synonyms:(2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

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Chemical Property of (2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

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Technology Process of (2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

There total 1 articles about (2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 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:

: 219864-81-0
Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5,6-bis-benzyloxy-tetrahydro-pyran-4-yl ester

: 219864-84-3
(2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Guidance literature:: With sodium methylate; In methanol; for 6h; Yield given; Ambient temperature;
DOI:10.1021/jo981477k

Reference yield:

: 219864-84-3
(2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

: (2S,3S,4S,5R,6R)-5,6-Bis-benzyloxy-3,4-dihydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide; In tetrahydrofuran; at 0 ℃; for 0.333333h;
DOI:10.1021/jo981477k

Reference yield:

: 219864-84-3
(2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

: 219864-92-3
(1S,3R,4R,5R,6S)-5-Benzoyloxy-3,4-bis-benzyloxy-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: NaHCO₃, KBr, TEMPO, NaOCl / tetrahydrofuran / 0.33 h / 0 °C

2: IR-120(H⁺) / 12 h / Ambient temperature

3: pyridine / 5 h / Ambient temperature

4: DBU / CH₂Cl₂ / 15 h / Ambient temperature

5: 64 percent / NBS / tetrahydrofuran; H₂O / Ambient temperature

6: 85 percent / Ag₂O / dimethylformamide; tetrahydrofuran / 15 h / Ambient temperature

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; N-Bromosuccinimide; IR-120(H⁺); sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium bromide; silver(l) oxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo981477k