(1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol

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Chemical Name:(1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol
CAS No.:181262-69-1
Molecular Formula:C₃₃H₄₄O₉
Molecular Weight:584.707
Hs Code.:

(1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol

Synonyms:(1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol

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Chemical Property of (1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol

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Technology Process of (1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol

There total 21 articles about (1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-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:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 181262-69-1
(1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / p-TsOH / dimethylformamide / 12 h / 23 °C

2: 1.) NaH, CS₂, MeI, 2.) n-Bu₃SnH, AIBN / 1.) THF, 23 deg C, 30 min, 2.) toluene, 110 deg C, 1 h

3: 98 percent / DIBAL / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4: 98 percent / I₂, Ph₃P, imidazole / benzene / 3 h / 70 °C

5: DBU / 1,2-dichloro-benzene / 0.25 h / 200 °C

6: 1.) O₃, 2.) DMS / 1.) MeOH, -78 deg C, 2.) MeOH, 23 deg C, 1 h

7: 1.) n-BuLi / 1.) THF, from -78 deg C to 0 deg C, 70 min, 2.) THF, from -78 deg C to 23 deg C

8: Et₃SiH, BF₃*Et₂O / CH₂Cl₂; acetonitrile / 0.5 h / -25 °C

9: H₂ / Lindlar catalyst / ethyl acetate / 0.83 h

10: OsO₄, NMO / 2-methyl-propan-2-ol; acetone; H₂O / 12 h / 23 °C

With 1H-imidazole; triethylsilane; carbon disulfide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); 2,3-dimercapto-succinic acid; boron trifluoride diethyl etherate; hydrogen; iodine; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; methyl iodide; Lindlar's catalyst; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/ja961230+

Reference yield:

: 82598-84-3
2,3,4,6-tetra-O-benzyl-D-galactonolactone

: 181262-69-1
(1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol

Guidance literature:: Multi-step reaction with 16 steps

1: diethyl ether / 0.25 h / -78 °C

2: Et₃SiH, BF₃*Et₂O / CH₂Cl₂; acetonitrile / 0.25 h / -20 °C

3: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂

4: 98 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

5: 100 percent / H₂ / Pd(OH)2/C / methanol / 4 h / 23 °C

6: 74 percent / NaH / dimethylformamide / 12 h / 23 °C

7: 97 percent / p-TsOH / dimethylformamide / 12 h / 23 °C

8: 1.) NaH, CS₂, MeI, 2.) n-Bu₃SnH, AIBN / 1.) THF, 23 deg C, 30 min, 2.) toluene, 110 deg C, 1 h

9: 98 percent / DIBAL / CH₂Cl₂ / 1.5 h / -78 - 0 °C

10: 98 percent / I₂, Ph₃P, imidazole / benzene / 3 h / 70 °C

11: DBU / 1,2-dichloro-benzene / 0.25 h / 200 °C

12: 1.) O₃, 2.) DMS / 1.) MeOH, -78 deg C, 2.) MeOH, 23 deg C, 1 h

13: 1.) n-BuLi / 1.) THF, from -78 deg C to 0 deg C, 70 min, 2.) THF, from -78 deg C to 23 deg C

14: Et₃SiH, BF₃*Et₂O / CH₂Cl₂; acetonitrile / 0.5 h / -25 °C

15: H₂ / Lindlar catalyst / ethyl acetate / 0.83 h

16: OsO₄, NMO / 2-methyl-propan-2-ol; acetone; H₂O / 12 h / 23 °C

With 1H-imidazole; triethylsilane; carbon disulfide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); 2,3-dimercapto-succinic acid; boron trifluoride diethyl etherate; hydrogen; iodine; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; methyl iodide; palladium dihydroxide; Lindlar's catalyst; In methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/ja961230+

Reference yield:

: 181491-12-3
(2R,3R,4S,4aR,8aS)-2-Hydroxymethyl-octahydro-pyrano[3,2-b]pyran-3,4-diol

: 181262-69-1
(1R,2R)-3-((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-1-((2S,3R,4aR,8aS)-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / p-TsOH / dimethylformamide / 12 h / 23 °C

2: 1.) NaH, CS₂, MeI, 2.) n-Bu₃SnH, AIBN / 1.) THF, 23 deg C, 30 min, 2.) toluene, 110 deg C, 1 h

3: 98 percent / DIBAL / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4: 98 percent / I₂, Ph₃P, imidazole / benzene / 3 h / 70 °C

5: DBU / 1,2-dichloro-benzene / 0.25 h / 200 °C

6: 1.) O₃, 2.) DMS / 1.) MeOH, -78 deg C, 2.) MeOH, 23 deg C, 1 h

7: 1.) n-BuLi / 1.) THF, from -78 deg C to 0 deg C, 70 min, 2.) THF, from -78 deg C to 23 deg C

8: Et₃SiH, BF₃*Et₂O / CH₂Cl₂; acetonitrile / 0.5 h / -25 °C

9: H₂ / Lindlar catalyst / ethyl acetate / 0.83 h

10: OsO₄, NMO / 2-methyl-propan-2-ol; acetone; H₂O / 12 h / 23 °C

With 1H-imidazole; triethylsilane; carbon disulfide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); 2,3-dimercapto-succinic acid; boron trifluoride diethyl etherate; hydrogen; iodine; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; methyl iodide; Lindlar's catalyst; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/ja961230+