Acetic acid (2S,3R)-2-((3S,4aR,8aS)-3-benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R)-2-((3S,4aR,8aS)-3-benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 440083-27-2
• Molecular Formula: C₂₅H₃₂O₇
• Molecular Weight: 444.525
• Mol file: 440083-27-2.mol

Synonyms:Acetic acid (2S,3R)-2-((3S,4aR,8aS)-3-benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R)-2-((3S,4aR,8aS)-3-benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R)-2-((3S,4aR,8aS)-3-benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-yl ester

There total 23 articles about Acetic acid (2S,3R)-2-((3S,4aR,8aS)-3-benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-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: 98.0%

acetic anhydride (108-24-7) + (2S,3R)-2-((3S,4aR,8aS)-3-Benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-ol (440083-26-1) → Acetic acid (2S,3R)-2-((3S,4aR,8aS)-3-benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-yl ester (440083-27-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 6h;

DOI:10.1016/S0040-4020(02)00047-9

Reference yield:

2-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)acetaldehyde (125878-02-6) → Acetic acid (2S,3R)-2-((3S,4aR,8aS)-3-benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-yl ester (440083-27-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 88 percent / NaH / benzene / 0.25 h / 25 °C

2.1: 98 percent / DIBALH / diethyl ether / 1.5 h / 0 °C

3.1: 95 percent / tBuOOH; (+)-DET; 4 Angstroem molecular sieves / CH₂Cl₂ / 12 h / -20 °C

4.1: 93 percent / Et₃N; 4-DAMP / CH₂Cl₂ / 8 h / 25 °C

5.1: 97 percent / NaI; NaHCO₃ / butan-2-one / 1 h / 60 °C

6.1: 99 percent / tBuLi / diethyl ether / 2 h / -78 °C

7.1: 96 percent / (iPr)2EtN; 4-DAMP / CH₂Cl₂ / 6 h / 25 °C

8.1: 75 percent / NMO; OsO₄ / tetrahydrofuran; H₂O; acetone / 12 h / 25 °C

9.1: TBAF / tetrahydrofuran / 6 h / 25 °C

10.1: (n-Bu)4NIO₄ / methanol; H₂O / 3 h / 20 °C

11.1: 73 percent / PCC; NaOAc / CH₂Cl₂ / 6 h / 25 °C

12.1: n-BuLi / tetrahydrofuran / 1 h / -35 °C

12.2: 93 percent / tetrahydrofuran / 1.5 h / 25 °C

13.1: 96 percent / CSA / 12 h / 25 °C

14.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 25 °C

With tert.-butylhydroperoxide; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium acetate; 4-diphenylacetoxy-N-methylpiperidine methiodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; tetrabutylammonium periodite; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; butanone; benzene;

DOI:10.1016/S0040-4020(02)00047-9

Reference yield:

(E)-6-[(tert-butyldimethylsilyl)oxy]-2-hexen-1-ol (98897-64-4) → Acetic acid (2S,3R)-2-((3S,4aR,8aS)-3-benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-yl ester (440083-27-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / t-BuOOH; (-)-DET; (iPrO)4Ti / CH₂Cl₂ / 3 h

2.1: 91 percent / NMO; TPAP / CH₂Cl₂

3.1: 78 percent / PPh₃; Et₃N / CH₂Cl₂

4.1: 98 percent / TBAF / tetrahydrofuran / 3 h

5.1: 93 percent / CSA / CH₂Cl₂ / 0 - 25 °C

6.1: 96 percent / imidazole / CH₂Cl₂

7.1: n-BuLi / tetrahydrofuran / 1 h / -35 °C

7.2: 93 percent / tetrahydrofuran / 1.5 h / 25 °C

8.1: 96 percent / CSA / 12 h / 25 °C

9.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; (-)-diethyl tartrate; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(02)00047-9

upstream raw materials:

acetic anhydride

(2S,3R)-2-((3S,4aR,8aS)-3-Benzyloxy-2-methoxy-octahydro-pyrano[3,2-b]pyran-2-ylethynyl)-tetrahydro-pyran-3-ol

2-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)acetaldehyde

(E)-6-[(tert-butyldimethylsilyl)oxy]-2-hexen-1-ol