(2R,3R,4S,5R,6R)-2-((S)-3-Allyloxy-2-benzyloxymethoxy-propoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

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Chemical Name:(2R,3R,4S,5R,6R)-2-((S)-3-Allyloxy-2-benzyloxymethoxy-propoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
CAS No.:112146-72-2
Molecular Formula:C₂₀H₃₀O₉
Molecular Weight:414.453
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-2-((S)-3-Allyloxy-2-benzyloxymethoxy-propoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

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Chemical Property of (2R,3R,4S,5R,6R)-2-((S)-3-Allyloxy-2-benzyloxymethoxy-propoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

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Technology Process of (2R,3R,4S,5R,6R)-2-((S)-3-Allyloxy-2-benzyloxymethoxy-propoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

There total 5 articles about (2R,3R,4S,5R,6R)-2-((S)-3-Allyloxy-2-benzyloxymethoxy-propoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-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:

: 112146-71-1
Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((S)-3-allyloxy-2-benzyloxymethoxy-propoxy)-tetrahydro-pyran-4-yl ester

: 112146-72-2
(2R,3R,4S,5R,6R)-2-((S)-3-Allyloxy-2-benzyloxymethoxy-propoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: With potassium tert-butylate; In 1,4-dioxane; methanol; at 20 ℃; for 2h; Yield given;
DOI:10.1016/S0040-4039(01)81041-8

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 112146-72-2
(2R,3R,4S,5R,6R)-2-((S)-3-Allyloxy-2-benzyloxymethoxy-propoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / N,N-diisopropylethylamine (DIPEA) / acetonitrile / 3 h / 40 °C

2: KOtBu / methanol; dioxane / 2 h / 20 °C

With potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; acetonitrile;
DOI:10.1016/S0040-4039(01)81041-8

Reference yield:

: 123-34-2,73485-54-8,90940-93-5,55941-86-1
(R)-3-allyloxypropane-1,2-diol

: 112146-72-2
(2R,3R,4S,5R,6R)-2-((S)-3-Allyloxy-2-benzyloxymethoxy-propoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 3 steps

1: 63 percent / Ag₂CO₃ / CH₂Cl₂ / -10 °C

2: 92 percent / N,N-diisopropylethylamine (DIPEA) / acetonitrile / 3 h / 40 °C

3: KOtBu / methanol; dioxane / 2 h / 20 °C

With potassium tert-butylate; N-ethyl-N,N-diisopropylamine; silver carbonate; In 1,4-dioxane; methanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(01)81041-8