1L-(1,2,3/4)-4-Azido-1-O-(4-methoxybenzyl)-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol

Base Information

Chemical Name:1L-(1,2,3/4)-4-Azido-1-O-(4-methoxybenzyl)-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol
CAS No.:137423-19-9
Molecular Formula:C₁₈H₂₅N₃O₆
Molecular Weight:379.413
Hs Code.:

Synonyms:1L-(1,2,3/4)-4-Azido-1-O-(4-methoxybenzyl)-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol

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Chemical Property of 1L-(1,2,3/4)-4-Azido-1-O-(4-methoxybenzyl)-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol

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Technology Process of 1L-(1,2,3/4)-4-Azido-1-O-(4-methoxybenzyl)-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol

There total 6 articles about 1L-(1,2,3/4)-4-Azido-1-O-(4-methoxybenzyl)-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol 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: 60.0%

: 137423-18-8
2L-(1,2,3/4)-4-Azido-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol

: 824-94-2
p-methoxybenzyl chloride

: 137423-19-9
1L-(1,2,3/4)-4-Azido-1-O-(4-methoxybenzyl)-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(91)80030-A

Reference yield:

: 53437-75-5
methyl 2-amino-6-bromo-2,6-dideoxy-α-D-altropyranoside

: 137423-19-9
1L-(1,2,3/4)-4-Azido-1-O-(4-methoxybenzyl)-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 1) iPr₂NEt, 2) DBU / 1) CH₂Cl₂, 15 h, reflux, 2) toluene, 15 h, reflux

2: 5.75 g / Hg(OCOCF₃)2 / acetone; H₂O / 20 h / Ambient temperature

3: 69 percent / Et₃N, MeSO₂Cl / CH₂Cl₂ / 1.5 h / 0 °C

4: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / 0 °C

5: 1) NaH / 1) DMF, 0 deg C, 30 min, 2) r.t., 18 h

With sodium tetrahydroborate; cerium(III) chloride; sodium hydride; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; mercury(II) trifluoroacetate; In methanol; dichloromethane; water; acetone;
DOI:10.1021/jo00068a045

Reference yield:

: 137423-15-5
Methyl 2-azido-2,6-dideoxy-3,4-bis-O-(methoxymethyl)-α-D-arabino-5-enopyranoside

: 137423-19-9
1L-(1,2,3/4)-4-Azido-1-O-(4-methoxybenzyl)-2,3-bis-O-(methoxymethyl)-5-cyclohexene-1,2,3-triol

Guidance literature:: Multi-step reaction with 4 steps

1: 5.75 g / Hg(OCOCF₃)2 / acetone; H₂O / 20 h / Ambient temperature

2: 69 percent / Et₃N, MeSO₂Cl / CH₂Cl₂ / 1.5 h / 0 °C

3: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / 0 °C

4: 1) NaH / 1) DMF, 0 deg C, 30 min, 2) r.t., 18 h

With sodium tetrahydroborate; cerium(III) chloride; sodium hydride; methanesulfonyl chloride; triethylamine; mercury(II) trifluoroacetate; In methanol; dichloromethane; water; acetone;
DOI:10.1021/jo00068a045