(3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

Base Information

Chemical Name:(3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene
CAS No.:728900-06-9
Molecular Formula:C₃₆H₃₇N₃O₅
Molecular Weight:591.707
Hs Code.:

Synonyms:(3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

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Chemical Property of (3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

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Technology Process of (3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

There total 10 articles about (3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene 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: 59.0%

: 728900-15-0
(3R,4S,5R,6S)-3-acetoxy-4,6-di(benzyloxy)-3-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

: 728900-06-9
(3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

Guidance literature:: With sodium azide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; for 2h; Heating;
DOI:10.1071/CH03203

Reference yield:

: 728900-13-8
(4S,5R,6S)-4,6-di(benzyloxy)-5-[(4-methoxybenzyl)oxy]cyclohex-2-enone

: 728900-06-9
(3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

Guidance literature:: Multi-step reaction with 3 steps

1.1: Mg; HgCl₂ / tetrahydrofuran / 1.5 h / 0 °C

1.2: 64 percent / tetrahydrofuran / 1.5 h / 0 °C

2.1: 82 percent / pyridine; 4-(dimethylamino)pyridine

3.1: 59 percent / NaN₃ / Pd(PPh₃)4 / tetrahydrofuran; H₂O / 2 h / Heating

With pyridine; dmap; sodium azide; magnesium; mercury dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water;
DOI:10.1071/CH03203

Reference yield:

: 202648-54-2
methyl 2-O-benzyl-3-O-(4-methoxybenzyl)-α-D-glucopyranoside

: 728900-06-9
(3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 87 percent / I₂; imidazole; Ph₃P / toluene / 1 h / 70 °C

2.1: 82 percent / NaH / dimethylformamide; various solvent(s) / 18 h

3.1: Hg(OCOCF₃)2 / acetone; H₂O / 12 h

3.2: 80 percent / MsCl; Et₃N / CH₂Cl₂ / 1 h / 20 °C

4.1: Mg; HgCl₂ / tetrahydrofuran / 1.5 h / 0 °C

4.2: 64 percent / tetrahydrofuran / 1.5 h / 0 °C

5.1: 82 percent / pyridine; 4-(dimethylamino)pyridine

6.1: 59 percent / NaN₃ / Pd(PPh₃)4 / tetrahydrofuran; H₂O / 2 h / Heating

With pyridine; 1H-imidazole; dmap; sodium azide; iodine; mercury(II) trifluoroacetate; sodium hydride; magnesium; triphenylphosphine; mercury dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1071/CH03203