benzyl (1S,3R,4S,5R,6R)-4,5-dihydroxy-6-(methoxymethoxy)cyclohexane-1,3-diyldicarbamate

Base Information

• Chemical Name: benzyl (1S,3R,4S,5R,6R)-4,5-dihydroxy-6-(methoxymethoxy)cyclohexane-1,3-diyldicarbamate
• CAS No.: 1554421-34-9
• Molecular Formula: C₂₄H₃₀N₂O₈
• Molecular Weight: 474.511

Synonyms:benzyl (1S,3R,4S,5R,6R)-4,5-dihydroxy-6-(methoxymethoxy)cyclohexane-1,3-diyldicarbamate

Chemical Property of benzyl (1S,3R,4S,5R,6R)-4,5-dihydroxy-6-(methoxymethoxy)cyclohexane-1,3-diyldicarbamate

Chemical Property:

Purity/Quality:

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Technology Process of benzyl (1S,3R,4S,5R,6R)-4,5-dihydroxy-6-(methoxymethoxy)cyclohexane-1,3-diyldicarbamate

There total 2 articles about benzyl (1S,3R,4S,5R,6R)-4,5-dihydroxy-6-(methoxymethoxy)cyclohexane-1,3-diyldicarbamate 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: 88.0%

C30H38N2O8 (1554421-36-1) → benzyl (1S,3R,4S,5R,6R)-4,5-dihydroxy-6-(methoxymethoxy)cyclohexane-1,3-diyldicarbamate (1554421-34-9)

Guidance literature:

With acetic acid; In water; at 23 ℃; for 1.5h;

DOI:10.1016/j.bmcl.2013.12.125

Reference yield:

dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate (82509-76-0) → benzyl (1S,3R,4S,5R,6R)-4,5-dihydroxy-6-(methoxymethoxy)cyclohexane-1,3-diyldicarbamate (1554421-34-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

1.2: 16 h / 23 °C / Inert atmosphere

2.1: acetic acid / water / 1.5 h / 23 °C

With tetra-(n-butyl)ammonium iodide; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane; water;

DOI:10.1016/j.bmcl.2013.12.125

Reference yield: 51.0%

benzyl (1S,3R,4S,5R,6R)-4,5-dihydroxy-6-(methoxymethoxy)cyclohexane-1,3-diyldicarbamate (1554421-34-9) → benzyl (3aR,5S,6R,7S,7aS)-7-hydroxy-6-(methoxymethoxy)-2-oxooctahydro-benzo[d]oxazol-5-ylcarbamate (1554421-38-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 23 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2013.12.125

upstream raw materials:

dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

C₃₀H₃₈N₂O₈

Downstream raw materials:

(1R,2R,3S,4R,6S)-4-amino-6-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)cyclohex-ane-1,2,3-triol

(S)-4-amino-2-hydroxy-N-((1R,2S,3R,4R,5S)-2,3,4-trihydroxy-5-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)cyclohexyl)butanamide

C₈H₁₆N₄O₄

C₁₁H₂₀N₄O₅

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