(2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol
CAS No.:669053-62-7
Molecular Formula:C₁₆H₂₄O₇S
Molecular Weight:360.428
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol

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Chemical Property of (2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol

Chemical Property:

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Technology Process of (2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol

There total 1 articles about (2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol 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%

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 107-30-2
chloromethyl methyl ether

: 669053-62-7
(2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;
DOI:10.1016/j.tetlet.2003.11.006

Reference yield:

: 669053-62-7
(2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol

: nonamethylcorilagin

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / 0.5 h / 0 °C

1.2: dimethylformamide / 2.5 h / 0 - 20 °C

2.1: NBS / tetrahydrofuran; H₂O / 0.33 h / 0 °C

3.1: 82 percent / tetrahydrofuran / -50 - 20 °C

4.1: NaH / 1 h / 20 °C

4.2: dimethylformamide / 7 h / 20 °C

5.1: HCl / propan-2-ol / 3 h / 60 °C

6.1: 94 percent / EDCI (WSC); DMAP / CH₂Cl₂ / 10 h / 20 °C

7.1: 48 percent / Cu / dimethylformamide / 22 h / Heating

8.1: 85 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

9.1: 70 percent / NaIO₄; OsO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

10.1: Et₃N / CH₂Cl₂ / 15 h / 20 °C

11.1: 92 percent / H₂ / Pd(OH)2/C / tetrahydrofuran / 4 h

With hydrogenchloride; dmap; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; hydrogen; copper; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; 3.1: Wittig olefination / 7.1: Ullmann coupling;
DOI:10.1016/j.tetlet.2003.11.006

Reference yield:

: 100-39-0
benzyl bromide

: 669053-62-7
(2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol

: (2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-4-methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran

Guidance literature:: (2R,3R,4S,5R,6S)-4-Methoxymethoxy-2-methoxymethoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol; With sodium hydride; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2.5h; Further stages.;
DOI:10.1016/j.tetlet.2003.11.006