(2R,4R,4aR,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-tetrahydro-pyrano[2,3-b]pyran-3-one

Base Information

• Chemical Name: (2R,4R,4aR,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-tetrahydro-pyrano[2,3-b]pyran-3-one
• CAS No.: 128041-89-4
• Molecular Formula: C₄₇H₆₀O₈Si
• Molecular Weight: 781.074

Synonyms:

Chemical Property of (2R,4R,4aR,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-tetrahydro-pyrano[2,3-b]pyran-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,4aR,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-tetrahydro-pyrano[2,3-b]pyran-3-one

There total 3 articles about (2R,4R,4aR,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-tetrahydro-pyrano[2,3-b]pyran-3-one 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:

2,3,5,9-tetra-O-benzyl-4,8-dideoxy-4-C-(1'-formyl)-(1'S)-2,8-di-C-methyl-L-talo-L-altro-1',1-bipyranoside-decitol (128062-05-5) → (2R,4R,4aR,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-tetrahydro-pyrano[2,3-b]pyran-3-one (128041-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / triethylamin, 2,4-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

2: 1) DMSO, oxalyl chloride / 1) CH₂Cl₂, -78 deg C, 2) a) 25 min, b) Et₃N

With oxalyl dichloride; 2,4-dimethylaminopyridine; dimethyl sulfoxide; triethylamine; In dichloromethane;

Reference yield:

(3S,4S,4aS,6R,7R,8S,8aR,9aS,10R,10aS)-3,4,6,10-Tetrakis-benzyloxy-7-(3,4-dimethyl-benzyloxy)-3,8-dimethyl-decahydro-1,5,9-trioxa-anthracene → (2R,4R,4aR,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-tetrahydro-pyrano[2,3-b]pyran-3-one (128041-89-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, H₂O, 2) NaBH₄ / 1) a) CH₂Cl₂, p-dioxane, r.t., 4h, b) 3,4-dimethoxybenzylalcohol 2) EtOH, r.t., 12h

2: 75 percent / triethylamin, 2,4-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

3: 1) DMSO, oxalyl chloride / 1) CH₂Cl₂, -78 deg C, 2) a) 25 min, b) Et₃N

With sodium tetrahydroborate; oxalyl dichloride; 2,4-dimethylaminopyridine; water; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

Reference yield:

(2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol (123505-98-6) → (2R,4R,4aR,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-tetrahydro-pyrano[2,3-b]pyran-3-one (128041-89-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; Yield given. Multistep reaction; 1) CH₂Cl₂, -78 deg C, 2) a) 25 min, b) Et₃N;

upstream raw materials:

(2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

2,3,5,9-tetra-O-benzyl-4,8-dideoxy-4-C-(1'-formyl)-(1'S)-2,8-di-C-methyl-L-talo-L-altro-1',1-bipyranoside-decitol

Downstream raw materials:

2,3,5,9-tetra-O-benzyl-4,6,8-trideoxy-4-C-(1'-formyl)-(1'S)-2,8-di-C-methyl-10-O-t-butyldimethylsilyl-L-lyxo-L-altro-6-eno-1',1-bipyranoside-decitol

2,3,5,9-tetra-O-benzyl-4,6,8-10,11-pentadeoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-L-galacto-L-altro-1,1':1',7-bipyranoside-undecitol

2,3,5,9-tetra-O-benzyl-4,6,8-trideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2,8-di-C-methyl-L-galacto-L-altro-1',1-bipyranoside-decitol

2,3,5,9-tetra-O-benzyl-4,6,8,11-tetradeoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2,8-di-C-methyl-L-galacto-L-altro-10-ulo-1',1-bipyranoside-decitol

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