Methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-15-methyl-hexadecyl ester

Base Information

Chemical Name:Methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-15-methyl-hexadecyl ester
CAS No.:160195-68-6
Molecular Formula:C₄₀H₅₈O₆S
Molecular Weight:666.963
Hs Code.:

Synonyms:Methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-15-methyl-hexadecyl ester

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Chemical Property of Methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-15-methyl-hexadecyl ester

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Technology Process of Methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-15-methyl-hexadecyl ester

There total 14 articles about Methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-15-methyl-hexadecyl 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: 100.0%

: 124-63-0
methanesulfonyl chloride

: 160195-61-9
(2R,3S,4R)-1,3,4-tribenzyloxy-16-methylheptadecan-2-ol

: 160195-68-6
Methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-15-methyl-hexadecyl ester

Guidance literature:: With dmap; In pyridine; for 3h; Ambient temperature;
DOI:10.1039/P19940002849

Reference yield:

: 160195-49-3
(2S,3R)-15-Methyl-hexadecane-1,2,3-triol

: 160195-68-6
Methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-15-methyl-hexadecyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 66 percent / pyridine / 5 h / 0 °C

2: 97 percent / PPTS / benzene / 0.5 h / Heating

3: 100 percent / LiOH*H₂O / methanol / 3 h / 50 °C

4: 97 percent / oxalyl dichloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -50 deg C, 2 h

5: 2.) TBAF / 1.) THF, room temperature, 2 h, 2.) 30 min

6: 99 percent / oxalyl dichloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -50 deg C, 30 min

7: 96 percent / cerium(III) chloride, NaBH₄ / methanol / 0.17 h / Ambient temperature

8: NaH / dimethylformamide / 2 h / Ambient temperature

9: 1.) MeI, 2.) NaBH₄, 3.) CuCl₂, CuO / 1.) MeCN, 50 deg C, 48 h, 2.) MeOH, room temperature, 30 min, 3.) MeCN, H₂O, room temeperature, 30 min

10: 61 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

11: 96 percent / PTSA / methanol / 3 h / Ambient temperature

12: 90 percent / NaH, TBAI / dimethylformamide / 1.) 50 deg C, 1 h, 2.) room temperature, 5 h

13: 84 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 0 °C

14: 100 percent / DMAP / pyridine / 3 h / Ambient temperature

With dmap; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(II) oxide; copper dichloride; methyl iodide; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1039/P19940002849

Reference yield:

: 160195-54-0
(2S,3R)-2,3-isopropylidenedioxy-15-methylhexadecan-1-ol

: 160195-68-6
Methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-15-methyl-hexadecyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 97 percent / oxalyl dichloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -50 deg C, 2 h

2: 2.) TBAF / 1.) THF, room temperature, 2 h, 2.) 30 min

3: 99 percent / oxalyl dichloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -50 deg C, 30 min

4: 96 percent / cerium(III) chloride, NaBH₄ / methanol / 0.17 h / Ambient temperature

5: NaH / dimethylformamide / 2 h / Ambient temperature

6: 1.) MeI, 2.) NaBH₄, 3.) CuCl₂, CuO / 1.) MeCN, 50 deg C, 48 h, 2.) MeOH, room temperature, 30 min, 3.) MeCN, H₂O, room temeperature, 30 min

7: 61 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

8: 96 percent / PTSA / methanol / 3 h / Ambient temperature

9: 90 percent / NaH, TBAI / dimethylformamide / 1.) 50 deg C, 1 h, 2.) room temperature, 5 h

10: 84 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 0 °C

11: 100 percent / DMAP / pyridine / 3 h / Ambient temperature

With dmap; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(II) oxide; copper dichloride; methyl iodide; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1039/P19940002849