(2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2H-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2H-pyran-2-carboxylic acid methyl ester
• CAS No.: 96720-61-5
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 96720-61-5.mol

Synonyms:(2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2H-pyran-2-carboxylic acid methyl ester

Chemical Property of (2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2H-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2H-pyran-2-carboxylic acid methyl ester

There total 22 articles about (2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2H-pyran-2-carboxylic acid methyl 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: 64.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + (2R,3S,6R)-6-((S)-2-Hydroxy-1-methyl-ethyl)-3-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid methyl ester (106930-30-7) → (2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2H-pyran-2-carboxylic acid methyl ester (96720-61-5)

Guidance literature:

With trifluorormethanesulfonic acid; In tetrachloromethane; cyclohexane; Ambient temperature;

DOI:10.1021/ja00241a028

Reference yield:

(2R,3S,4S)-4-Hydroxy-3-methyl-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester (106930-23-8) → (2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2H-pyran-2-carboxylic acid methyl ester (96720-61-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / pyridine / DMAP / 1 h

2: BF₃ etherate / various solvent(s) / -78 °C

3: OsO₄ / tetrahydrofuran / Ambient temperature

4: NaIO₄ / ethanol; H₂O / 2 h

5: NaBH₄ / ethanol / 0 deg C, RT, 35 min

6: 64 percent / trifluoromethanesulfonic acid / cyclohexane; CCl₄ / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; trifluorormethanesulfonic acid; dmap; boron trifluoride diethyl etherate; In tetrahydrofuran; tetrachloromethane; ethanol; cyclohexane; water;

DOI:10.1021/ja00241a028

Reference yield:

(2R,3R)-3-Methyl-4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester (106930-22-7) → (2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2H-pyran-2-carboxylic acid methyl ester (96720-61-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / cerium chloride heptahydrate, NaBH₄ / methanol; ethanol / 1 h / -78 °C

2: 95 percent / pyridine / DMAP / 1 h

3: BF₃ etherate / various solvent(s) / -78 °C

4: OsO₄ / tetrahydrofuran / Ambient temperature

5: NaIO₄ / ethanol; H₂O / 2 h

6: NaBH₄ / ethanol / 0 deg C, RT, 35 min

7: 64 percent / trifluoromethanesulfonic acid / cyclohexane; CCl₄ / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; trifluorormethanesulfonic acid; dmap; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; cyclohexane; water;

DOI:10.1021/ja00241a028

upstream raw materials:

diazomethane

(5S,6R)-5-<2-(benzyloxy)-1(S)-methyl>ethyl-6-<1(E)-propenyl>-1,4-dioxan-2-one

O-benzyl 2,2,2-trichloroacetimidate

(2R,3S,6R)-6-((S)-2-Hydroxy-1-methyl-ethyl)-3-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

(2R,3S,6R)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-3-methyl-2-(1-oxopropyl)-2H-pyran

(2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-2-(1-hydroxypropyl)-3-methyl-2H-pyran