Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
CAS No.:175355-39-2
Molecular Formula:C₄₁H₅₁Br₂ClO₁₆
Molecular Weight:995.107
Hs Code.:

Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Synonyms:Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

There total 7 articles about Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 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: 87.0%

: 172975-30-3
Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester

: 175355-38-1
(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 175355-39-2
Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; for 0.05h;
DOI:10.1021/jo9520102

Reference yield:

: 100-39-0
benzyl bromide

: 175355-39-2
Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Bu₂SnO / 1.) MeOH, reflux, 1 h, 2.) DMF, 80 - 110 deg C, 2 h

2: 84 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 - 10 °C

3: 845 percent / Et₃SiH, CF₃CO₂H / CH₂Cl₂ / 2 h / 0 - 20 °C

4: 86 percent / Br₂, Et₄NBr / CH₂Cl₂ / 0 °C

5: 87 percent / N-iodosuccinimide, triethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.05 h

With pyridine; triethylsilane; N-iodo-succinimide; tetraethylammonium bromide; bromine; triethylsilyl trifluoromethyl sulfonate; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jo9520102

Reference yield:

: (4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 175355-39-2
Chloro-acetic acid (2S,3S,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-dibromo-pentyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 - 10 °C

2: 845 percent / Et₃SiH, CF₃CO₂H / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 86 percent / Br₂, Et₄NBr / CH₂Cl₂ / 0 °C

4: 87 percent / N-iodosuccinimide, triethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.05 h

With pyridine; triethylsilane; N-iodo-succinimide; tetraethylammonium bromide; bromine; triethylsilyl trifluoromethyl sulfonate; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jo9520102