2,3,5-tri-O-benzyl-4,6-dideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-aldehydo-D-talo-L-threo-1,1':1',7-bipyranoside-ocitol

Base Information

• Chemical Name: 2,3,5-tri-O-benzyl-4,6-dideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-aldehydo-D-talo-L-threo-1,1':1',7-bipyranoside-ocitol
• CAS No.: 128041-99-6
• Molecular Formula: C₃₄H₄₀O₈
• Molecular Weight: 576.687
• Mol file: 128041-99-6.mol

Synonyms:

Chemical Property of 2,3,5-tri-O-benzyl-4,6-dideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-aldehydo-D-talo-L-threo-1,1':1',7-bipyranoside-ocitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,5-tri-O-benzyl-4,6-dideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-aldehydo-D-talo-L-threo-1,1':1',7-bipyranoside-ocitol

There total 2 articles about 2,3,5-tri-O-benzyl-4,6-dideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-aldehydo-D-talo-L-threo-1,1':1',7-bipyranoside-ocitol 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:

((2S,3R,4S,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-methanol (128041-98-5) → 2,3,5-tri-O-benzyl-4,6-dideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-aldehydo-D-talo-L-threo-1,1':1',7-bipyranoside-ocitol (128041-99-6)

Guidance literature:

With Chloro-oxo-acetic acid; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1) CH2Cl2, -78 deg C, 20 min, 2) -78 deg C -> deg C;

Reference yield:

[(2S,3R,4S,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl]-methanol (114406-21-2) → 2,3,5-tri-O-benzyl-4,6-dideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-aldehydo-D-talo-L-threo-1,1':1',7-bipyranoside-ocitol (128041-99-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) N,N-di-isopropylethylamine, 2) CsF, 18-crown-6 / 1) CH₂Cl₂, 2) DMSO, 60 deg C, 1h

2: 1) DMSO, oxalylchloride, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 20 min, 2) -78 deg C -> deg C

With 18-crown-6 ether; Chloro-oxo-acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride;

Reference yield:

2,3,5-tri-O-benzyl-4,6-dideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-aldehydo-D-talo-L-threo-1,1':1',7-bipyranoside-ocitol (128041-99-6) → 2,3,5,9-tetra-O-benzyl-4,6,8-trideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-glycero-L-galacto-L-altro-1,1':1':7-bipyranoside-undecitol (128041-95-2,128112-21-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 2) DMSO, oxalylchloride, 3) Et₃N

2: 82 percent / tetrahydrofuran / Ambient temperature

3: 70 percent / 9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 1 h / Ambient temperature

4: 87 percent / pyridinium chlorochromate, Celite, NaOAc, Florisil / CH₂Cl₂ / 1 h / Ambient temperature

5: 2) NaH, tetrabutylammonium iodide / 1) THF, -90 -> 0 deg C, 2) DMF, 0 deg C, 20 min, 3) 0 deg C -> r.t., 1h

6: 80 percent / 1) O₃, 2) Me₂S / CH₂Cl₂

7: 72 percent / tetrahydrofuran / -78 °C

8: 1) O₃, MeOH, 2) Me₂S / 1) CH₂Cl₂, -78 deg C to r.t., 30 min, 2) 30 min

9: NaBH₄ / ethanol / 0.08 h / 0 °C

With methanol; sodium tetrahydroborate; florisil; 9-borabicyclo[3.3.1]nonane dimer; dimethylsulfide; Chloro-oxo-acetic acid; Celite; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane;

upstream raw materials:

((2S,3R,4S,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-methanol

[(2S,3R,4S,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl]-methanol

Downstream raw materials:

2,3,5-tri-O-benzyl-4,6,9-trideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-ulo-D-talo-L-threo-1,1':1',7-bipyranoside-nonitol

2,3,5-tri-O-benzyl-4,6,8,9-tetradeoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2,8-di-C-methyl-D-talo-L-threo-8-eno-1,1':1',7-bipyranoside-nonitol

(R)-2-((2S,3R,4S,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-propionaldehyde

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