(S)-methyl 11-hydroxyhexadecanoate

Base Information

• Chemical Name: (S)-methyl 11-hydroxyhexadecanoate
• CAS No.: 121043-05-8
• Molecular Formula: C₁₇H₃₄O₃
• Molecular Weight: 286.455
• Mol file: 121043-05-8.mol

Synonyms:(S)-methyl 11-hydroxyhexadecanoate

Chemical Property of (S)-methyl 11-hydroxyhexadecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 11-hydroxyhexadecanoate

There total 6 articles about (S)-methyl 11-hydroxyhexadecanoate 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:

operculinic acid A methyl ester → D-Fucose (3615-37-0,478518-52-4) + L-Rhamnose (3615-41-6,478518-52-4) + D-glucose (50-99-7) + (S)-methyl 11-hydroxyhexadecanoate (121043-05-8)

Guidance literature:

With sulfuric acid;

DOI:10.1080/14786419.2015.1030739

Reference yield:

9-bromononan-1-ol (55362-80-6) → (S)-methyl 11-hydroxyhexadecanoate (121043-05-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: magnesium; I₂ / tetrahydrofuran / 2 h / Heating

2.2: 66 percent / CuI / tetrahydrofuran / 2.5 h / -78 - 20 °C

3.1: 90.5 percent / pyridine / 20 °C

4.1: 89.4 percent / Jones reagent / acetone / 1.5 h / 0 - 20 °C

5.1: 96.9 percent / BF₃*OEt₂ / 4 h / 40 °C

With pyridine; 1H-imidazole; dmap; jones reagent; boron trifluoride diethyl etherate; iodine; magnesium; In tetrahydrofuran; dichloromethane; acetone; 1.1: silylation / 2.1: Metallation / 2.2: Addition / 3.1: Acetylation / 4.1: Jones oxidation / 5.1: methanolysis;

DOI:10.1021/jo9711450

Reference yield:

merremoside j methyl ester (182121-34-2) → methyl D-glucopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6,3149-68-6) + (S)-methyl 11-hydroxyhexadecanoate (121043-05-8) + methyl L-rhamnopyranoside (1128-40-1,1198-82-9,2592-55-4,5155-43-1,6340-52-9,10503-91-0,14009-07-5,14687-15-1,14917-55-6,15814-59-2,24332-98-7,34299-65-5,42214-00-6,42214-11-9,57783-34-3,57783-36-5,57783-38-7,57783-40-1,57783-42-3,58525-46-5,58525-47-6,58525-48-7,62182-01-8,62182-02-9,65310-00-1,65941-62-0,68069-80-7,71116-57-9,72274-54-5,72274-55-6,73036-22-3,83198-64-5,85505-15-3,102517-74-8,109718-80-1,109718-81-2,125280-09-3,129172-95-8,63864-94-8)

Guidance literature:

With hydrogenchloride; In methanol; for 1h; Heating;

DOI:10.1248/cpb.44.1693

upstream raw materials:

methanol

(+)-11-hydroxy-hexadecanoic acid

merremoside c

merremoside i methyl ester

Downstream raw materials:

C₃₈H₆₀O₁₀

1-(hydroxycarbonyl)pentadec-10(S)-yl 4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl ester

1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside