Dithiocarbonic acid O-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl) ester S-methyl ester

Base Information

Chemical Name:Dithiocarbonic acid O-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl) ester S-methyl ester
CAS No.:181267-59-4
Molecular Formula:C₃₀H₃₄O₆S₂
Molecular Weight:554.728
Hs Code.:

Dithiocarbonic acid O-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl) ester S-methyl ester

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Chemical Property of Dithiocarbonic acid O-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl) ester S-methyl ester

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Technology Process of Dithiocarbonic acid O-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl) ester S-methyl ester

There total 1 articles about Dithiocarbonic acid O-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl) ester S-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:

: 75-15-0,12122-00-8
carbon disulfide

: 35303-86-7
(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol

: 74-88-4
methyl iodide

: 181267-59-4
Dithiocarbonic acid O-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl) ester S-methyl ester

Guidance literature:: carbon disulfide; (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol; With sodium hydride; In tetrahydrofuran;

methyl iodide; With 1H-imidazole; In tetrahydrofuran; at 0 - 20 ℃; for 1h;
DOI:10.1055/s-2001-11398

Reference yield:

: 181267-59-4
Dithiocarbonic acid O-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl) ester S-methyl ester

: (2R,3S,4aR,5aS,6aR,10aS,11aR,12aS)-3-Benzyloxy-2-benzyloxymethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacene

Guidance literature:: Multi-step reaction with 23 steps

1.1: Bu₃SnH; AIBN / toluene / 36 h / 110 °C

2.1: 69 percent / aq. HCl / acetic acid / 48 h / 60 °C

3.1: 70 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

4.1: tetrahydrofuran / 1 h / -78 °C

5.1: Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 2 h / 0 °C

6.1: 100 percent / Na; NH₃ / tetrahydrofuran / 2 h / -60 °C

7.1: 60 percent / POCl₃; DMF / 12 h / 20 °C

8.1: 96 percent / imidazole / CH₂Cl₂ / 48 h / 20 °C

9.1: 4-methylmorpholine N-oxide; OsO₄; H₂O / tetrahydrofuran / 12 h / 20 °C

10.1: aq.NaIO₄ / methanol / 0 °C

11.1: 97 percent / Ph₃P; Et₃N / CH₂Cl₂; hexane / 3 h / 0 °C

12.1: 65 percent / BuLi / tetrahydrofuran / 2 h / -78 °C

13.1: 98 percent / BuLi / tetrahydrofuran / 2 h / 0 °C

14.1: 89 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

15.1: 86 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 12 h / 20 °C

16.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 °C

17.1: O₃ / CH₂Cl₂ / 0.33 h / -78 °C

17.2: 60 percent / Ph₃P / CH₂Cl₂ / 1 h / 20 °C

18.1: 63 percent / H₂ / 10 percent Pd/C / ethyl acetate / 2 °C

19.1: 79 percent / K₂CO₃; MeOH / 2 h / 20 °C

20.1: 62 percent / NaH / dimethylformamide / 6 h / 0 °C

21.1: 66 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 3 h / 0 °C

22.1: 76 percent / NaH; nBu₄NI / tetrahydrofuran; dimethylformamide / 3 h / 25 °C

With 1H-imidazole; chromium dichloride; hydrogenchloride; methanol; triethylsilane; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; ammonia; water; hydrogen; tri-n-butyl-tin hydride; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; nickel dichloride; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-2001-11398