(2R,3S,5R,6S)-6-Allyl-2-((Z)-2-benzenesulfonyl-2-triethylsilanyl-vinyl)-5-benzyloxy-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,5R,6S)-6-Allyl-2-((Z)-2-benzenesulfonyl-2-triethylsilanyl-vinyl)-5-benzyloxy-tetrahydro-pyran-3-ol
• CAS No.: 552890-41-2
• Molecular Formula: C₂₉H₄₀O₅SSi
• Molecular Weight: 528.785

Synonyms:(2R,3S,5R,6S)-6-Allyl-2-((Z)-2-benzenesulfonyl-2-triethylsilanyl-vinyl)-5-benzyloxy-tetrahydro-pyran-3-ol

Chemical Property of (2R,3S,5R,6S)-6-Allyl-2-((Z)-2-benzenesulfonyl-2-triethylsilanyl-vinyl)-5-benzyloxy-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3S,5R,6S)-6-Allyl-2-((Z)-2-benzenesulfonyl-2-triethylsilanyl-vinyl)-5-benzyloxy-tetrahydro-pyran-3-ol

There total 31 articles about (2R,3S,5R,6S)-6-Allyl-2-((Z)-2-benzenesulfonyl-2-triethylsilanyl-vinyl)-5-benzyloxy-tetrahydro-pyran-3-ol 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: 85.0%

(2R,3S,5R,6S)-6-Allyl-5-benzyloxy-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-3-ol (617673-37-7) → (2R,3S,5R,6S)-6-Allyl-2-((Z)-2-benzenesulfonyl-2-triethylsilanyl-vinyl)-5-benzyloxy-tetrahydro-pyran-3-ol (552890-41-2)

Guidance literature:

With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

methyl 2-O-benzyl-3,6-dideoxy-α-D-ribo-hexopyranoside (50272-15-6) → (2R,3S,5R,6S)-6-Allyl-2-((Z)-2-benzenesulfonyl-2-triethylsilanyl-vinyl)-5-benzyloxy-tetrahydro-pyran-3-ol (552890-41-2)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 97 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: 87 percent / H₂SO₄ / 0.25 h / 0 °C

3.1: 66 percent / HCl / 1,2-dimethoxy-ethane; H₂O / 14 h / 55 °C

4.1: 93 percent / Ac₂O / dimethylsulfoxide / 14 h / 20 °C

5.1: diethyl ether / 0.5 h / -78 °C

6.1: 8.02 g / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0.33 h / -10 °C

7.1: 93 percent / NaOMe / methanol / 4 h / 20 °C

8.1: imidazole / dimethylformamide / 8 h / 20 °C

9.1: 7.72 g / CSA / methanol / 1 h / -10 °C

10.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

11.1: 91 percent / Ph₃P / CH₂Cl₂ / 0.33 h / 0 °C

12.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

12.2: 98 percent / tetrahydrofuran; hexane / 1 h / 0 °C

13.1: 83 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

14.1: 96 percent / DMAP / CH₂Cl₂ / 0.17 h / 20 °C

15.1: 100 percent / biscobalthexacarbonyl-2-methyl-but-3-yn-2-ol / 1,2-dichloro-ethane / 1.5 h / 60 °C

16.1: 97 percent / K₂CO₃ / methanol / 1.5 h / 20 °C

17.1: 85 percent / Na₂HPO₄; mCPBA / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; triethylsilane; dmap; disodium hydrogenphosphate; n-butyllithium; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; biscobalthexacarbonyl-2-methyl-but-3-yn-2-ol; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

methyl 4,6-O-isopropylidene-α-D-glucopyranoside (15354-29-7) → (2R,3S,5R,6S)-6-Allyl-2-((Z)-2-benzenesulfonyl-2-triethylsilanyl-vinyl)-5-benzyloxy-tetrahydro-pyran-3-ol (552890-41-2)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 68 percent / pyridine / CH₂Cl₂ / 48 h / 20 °C

2.1: CHCl₃; toluene / 1 h / 20 °C

2.2: toluene; CHCl₃ / 48 h / Heating

3.1: 5.32 g / NaH₂PO₂*H₂O; AIBN / 2-methoxy-ethanol / Heating

4.1: 93 percent / NaOMe / methanol; tetrahydrofuran / 0.75 h / 20 °C

5.1: KOH / 1 h / 110 °C

6.1: 32.0 g / Am,berlyst 15E(R) / methanol / 0.67 h / 20 °C

7.1: 97 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

8.1: 87 percent / H₂SO₄ / 0.25 h / 0 °C

9.1: 66 percent / HCl / 1,2-dimethoxy-ethane; H₂O / 14 h / 55 °C

10.1: 93 percent / Ac₂O / dimethylsulfoxide / 14 h / 20 °C

11.1: diethyl ether / 0.5 h / -78 °C

12.1: 8.02 g / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0.33 h / -10 °C

13.1: 93 percent / NaOMe / methanol / 4 h / 20 °C

14.1: imidazole / dimethylformamide / 8 h / 20 °C

15.1: 7.72 g / CSA / methanol / 1 h / -10 °C

16.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

17.1: 91 percent / Ph₃P / CH₂Cl₂ / 0.33 h / 0 °C

18.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

18.2: 98 percent / tetrahydrofuran; hexane / 1 h / 0 °C

19.1: 83 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

20.1: 96 percent / DMAP / CH₂Cl₂ / 0.17 h / 20 °C

21.1: 100 percent / biscobalthexacarbonyl-2-methyl-but-3-yn-2-ol / 1,2-dichloro-ethane / 1.5 h / 60 °C

22.1: 97 percent / K₂CO₃ / methanol / 1.5 h / 20 °C

23.1: 85 percent / Na₂HPO₄; mCPBA / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; triethylsilane; dmap; potassium hydroxide; disodium hydrogenphosphate; sodium hypophosphite; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); Am,berlyst 15E(R); sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; isobutyric Acid; biscobalthexacarbonyl-2-methyl-but-3-yn-2-ol; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; chloroform; 2-methoxy-ethanol; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(03)00873-1

upstream raw materials:

(2R,3S,5R,6S)-6-Allyl-5-benzyloxy-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-3-ol

methyl 2-O-benzyl-3,6-dideoxy-α-D-ribo-hexopyranoside

methyl-alpha-D-glucopyranoside

methyl 4,6-O-isopropylidene-α-D-glucopyranoside

Downstream raw materials:

C₃₅H₄₆O₈

(2S,5S,6S)-6-((2S,3R,4aS,6S,9S,9aR)-2-Allyl-9-benzenesulfonylmethyl-3-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl)-2-benzyloxy-5-methyl-heptane-1,4-diol

Acetic acid (2S,3S)-3-((2S,3R,4aS,6S,9S,9aR)-2-allyl-9-benzenesulfonylmethyl-3-benzyloxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-6-yl)-1-((S)-2-benzyloxy-3-hydroxy-propyl)-2-methyl-butyl ester

C₄₁H₅₀O₁₀S

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