(1S,3R)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-diol

Base Information

• Chemical Name: (1S,3R)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-diol
• CAS No.: 181489-09-8
• Molecular Formula: C₆₇H₈₀O₁₄
• Molecular Weight: 1109.36

Synonyms:(1S,3R)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-diol

Chemical Property of (1S,3R)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-diol

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Technology Process of (1S,3R)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-diol

There total 20 articles about (1S,3R)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-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:

(S)-4-Hydroxy-1-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-4-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butan-2-one (181489-07-6) → (1S,3S)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-diol (181488-65-3) + (1S,3R)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-diol (181489-09-8)

Guidance literature:

With sodium tris(acetoxy)borohydride; In acetic acid; acetonitrile; at 23 ℃; for 10h; Yield given. Yields of byproduct given;

DOI:10.1021/ja961230+

Reference yield:

(2R,3R,4R,5S,6R)-2-Allyl-6-methoxymethyl-tetrahydro-pyran-3,4,5-triol (181267-46-9) → (1S,3R)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-diol (181489-09-8)

Guidance literature:

Multi-step reaction with 18 steps

1: i-Pr₂NEt / CH₂Cl₂ / 23 °C

2: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, MeOH, -78 deg C

3: 1percent NiCl₂/CrCl₂ / tetrahydrofuran / 23 °C

4: pyridine

5: 67 percent / HF*pyridine / acetonitrile / 4 h / 0 °C

6: 81 percent / DBU / CH₂Cl₂ / 20 h

7: 89 percent / AgNO₃, imidazole / dimethylformamide

8: 95 percent / DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

9: 92 percent / pyridine / 0 °C

10: imidazole / dimethylformamide / 2 h / 23 °C

11: DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

12: 95 percent / I₂, Ph₃P, imidazole / benzene

13: 1.) (PhSe)2, NaBH₄, 2.) NaIO₄, i-Pr₂NH / 1.) EtOH, 23 deg C

14: n-Bu₄NF / tetrahydrofuran

15: NaH, n-Bu₄NI / dimethylformamide / 24 h / 23 °C

16: 1.) NCS, pyridine, 2.) i-Pr₂NEt / 1.) CHCl₃, 23 deg C, 1 h, 2.) CHCl₃, a) 0 deg C, 15 min, b) 60 deg C, 24 h

17: 80 percent / Mo(CO)6 / acetonitrile; H₂O / 80 °C

18: NaBH(OAc)3 / acetic acid; acetonitrile / 10 h / 23 °C

With pyridine; 1H-imidazole; chromium dichloride; sodium tetrahydroborate; sodium periodate; N-chloro-succinimide; hexacarbonyl molybdenum; diphenyl diselenide; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ja961230+

Reference yield:

(2R,3S,4R,5R,6R)-2-Allyl-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-methoxymethyl-tetrahydro-pyran (181263-09-2) → (1S,3R)-4-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-1-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butane-1,3-diol (181489-09-8)

Guidance literature:

Multi-step reaction with 17 steps

1: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, MeOH, -78 deg C

2: 1percent NiCl₂/CrCl₂ / tetrahydrofuran / 23 °C

3: pyridine

4: 67 percent / HF*pyridine / acetonitrile / 4 h / 0 °C

5: 81 percent / DBU / CH₂Cl₂ / 20 h

6: 89 percent / AgNO₃, imidazole / dimethylformamide

7: 95 percent / DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

8: 92 percent / pyridine / 0 °C

9: imidazole / dimethylformamide / 2 h / 23 °C

10: DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

11: 95 percent / I₂, Ph₃P, imidazole / benzene

12: 1.) (PhSe)2, NaBH₄, 2.) NaIO₄, i-Pr₂NH / 1.) EtOH, 23 deg C

13: n-Bu₄NF / tetrahydrofuran

14: NaH, n-Bu₄NI / dimethylformamide / 24 h / 23 °C

15: 1.) NCS, pyridine, 2.) i-Pr₂NEt / 1.) CHCl₃, 23 deg C, 1 h, 2.) CHCl₃, a) 0 deg C, 15 min, b) 60 deg C, 24 h

16: 80 percent / Mo(CO)6 / acetonitrile; H₂O / 80 °C

17: NaBH(OAc)3 / acetic acid; acetonitrile / 10 h / 23 °C

With pyridine; 1H-imidazole; chromium dichloride; sodium tetrahydroborate; sodium periodate; N-chloro-succinimide; hexacarbonyl molybdenum; diphenyl diselenide; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ja961230+

upstream raw materials:

(S)-4-Hydroxy-1-[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-4-((2R,3S,4aR,6R,7R,8S,8aS)-3,7,8-tris-benzyloxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-butan-2-one

C₆₇H₇₇NO₁₃

(2R,3R,4R,5S,6R)-2-Allyl-6-methoxymethyl-tetrahydro-pyran-3,4,5-triol

((2R,3S,4aR,6R,7S,8S,8aR)-3-Acetoxy-7,8-dihydroxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-acetic acid methyl ester

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