(R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol

Base Information

Chemical Name:(R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol
CAS No.:532401-52-8
Molecular Formula:C₂₆H₃₆O₈
Molecular Weight:476.567
Hs Code.:

Synonyms:(R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol

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Chemical Property of (R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol

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Technology Process of (R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol

There total 14 articles about (R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-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: 82.0%

: 532401-45-9
(2R,3R,4R,5R,6S)-3,4-Bis-benzyloxy-2-isopropoxy-5-methoxymethoxy-6-vinyl-tetrahydro-pyran

: 532401-52-8
(R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol

: (S)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol

Guidance literature:: With potassium osmate(VI); N-methyl-2-indolinone; In water; tert-butyl alcohol; at 20 ℃;
DOI:10.1246/cl.2003.190

Reference yield:

: 1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7
methyl ribofuranoside

: 532401-52-8
(R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine; DMAP / 20 °C

2: 20 percent / NaH / dimethylformamide / 20 °C

3: 90 percent / p-TsOH*H₂O / methanol / 20 °C

4: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

5: 60 percent / CSA / 48 h / 120 °C

6: 84 percent / NaH / tetrahydrofuran / 0 °C

7: 82 percent / K₂OsO₄*2H₂O; NMO / 2-methyl-propan-2-ol; H₂O / 20 °C

With pyridine; dmap; potassium osmate(VI); N-methyl-2-indolinone; oxalyl dichloride; camphor-10-sulfonic acid; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 4: Swern oxidation;
DOI:10.1246/cl.2003.190

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-Ribose

: 532401-52-8
(R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 9 steps

1: HCl / 0 °C

2: pyridine; DMAP / 20 °C

3: 20 percent / NaH / dimethylformamide / 20 °C

4: 90 percent / p-TsOH*H₂O / methanol / 20 °C

5: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

6: 60 percent / CSA / 48 h / 120 °C

7: 84 percent / NaH / tetrahydrofuran / 0 °C

8: 82 percent / K₂OsO₄*2H₂O; NMO / 2-methyl-propan-2-ol; H₂O / 20 °C

With pyridine; hydrogenchloride; dmap; potassium osmate(VI); N-methyl-2-indolinone; oxalyl dichloride; camphor-10-sulfonic acid; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 5: Swern oxidation;
DOI:10.1246/cl.2003.190