(R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid

Base Information

Chemical Name:(R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid
CAS No.:157459-92-2
Molecular Formula:C₃₉H₅₂O₈
Molecular Weight:648.837
Hs Code.:

Synonyms:(R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid

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Chemical Property of (R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid

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Technology Process of (R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid

There total 8 articles about (R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid 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: 84.0%

: 157459-93-3
(R)-3-((2R,3R,4S,5S,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-dodecanoic acid methyl ester

: 157459-92-2
(R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid

Guidance literature:: With lithium hydroxide; In methanol; diethyl ether; water; for 1h; Heating;
DOI:10.1016/S0040-4039(00)76898-5

Reference yield:

: 76835-64-8
methyl 3-oxododecanoate

: 157459-92-2
(R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / H₂ / RuCl₂<(R)-BINAP> / methanol / 40 h / 76000 Torr / Ambient temperature

2: 73 percent / molecular sieves 4A, 2-methyl-2-butene / zinc-p-tert-butylbenzoate / CH₂Cl₂ / 2.5 h / Ambient temperature

3: 84 percent / LiOH / methanol; H₂O; diethyl ether / 1 h / Heating

With lithium hydroxide; 2-methyl-but-2-ene; 4 A molecular sieve; hydrogen; RuCl₂[(R)-BINAP]; zinc(II) p-tert-butylbenzoate; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1016/S0040-4039(00)76898-5

Reference yield:

: 2771-55-3
2,3,4-tri-O-benzyl-D-galactopyranoside

: 157459-92-2
(R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine

2: piperidine

3: SOCl₂ / dimethylformamide

4: 73 percent / molecular sieves 4A, 2-methyl-2-butene / zinc-p-tert-butylbenzoate / CH₂Cl₂ / 2.5 h / Ambient temperature

5: 84 percent / LiOH / methanol; H₂O; diethyl ether / 1 h / Heating

With piperidine; pyridine; lithium hydroxide; thionyl chloride; 2-methyl-but-2-ene; 4 A molecular sieve; zinc(II) p-tert-butylbenzoate; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)76898-5