(1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol

Base Information

Chemical Name:(1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol
CAS No.:728900-14-9
Molecular Formula:C₃₆H₃₈O₆
Molecular Weight:566.694
Hs Code.:

Synonyms:(1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol

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Chemical Property of (1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol

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Technology Process of (1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol

There total 8 articles about (1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol 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: 64.0%

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

: 3587-60-8
Benzyloxymethyl chloride

: 728900-14-9
(1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol

Guidance literature:: Benzyloxymethyl chloride; With magnesium; mercury dichloride; In tetrahydrofuran; at 0 ℃; for 1.5h;

(4S,5R,6S)-4,6-di(benzyloxy)-5-[(4-methoxybenzyl)oxy]cyclohex-2-enone; In tetrahydrofuran; at 0 ℃; for 1.5h;
DOI:10.1071/CH03203

Reference yield:

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

: 728900-14-9
(1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 728900-08-1
methyl 2-O-benzyl-6-deoxy-6-iodo-3-O-(4-methoxybenzyl)-α-D-glucopyranoside

: 728900-14-9
(1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 82 percent / NaH / dimethylformamide; various solvent(s) / 18 h

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

2.2: 80 percent / MsCl; Et₃N / CH₂Cl₂ / 1 h / 20 °C

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

3.2: 64 percent / tetrahydrofuran / 1.5 h / 0 °C

With mercury(II) trifluoroacetate; sodium hydride; magnesium; mercury dichloride; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;
DOI:10.1071/CH03203