((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

Base Information

• Chemical Name: ((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
• CAS No.: 128041-98-5
• Molecular Formula: C₃₄H₄₂O₈
• Molecular Weight: 578.703
• Mol file: 128041-98-5.mol

Synonyms:

Chemical Property of ((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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((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

There total 1 articles about ((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 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-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl]-methanol (114406-21-2) + chloromethyl methyl ether (107-30-2) → ((2S,3R,4S,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-methanol (128041-98-5)

Guidance literature:

With 18-crown-6 ether; N-ethyl-N,N-diisopropylamine; cesium fluoride; Yield given. Multistep reaction; 1) CH₂Cl₂, 2) DMSO, 60 deg C, 1h;

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-4,6,8,9-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 (128042-01-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 2) DMSO, oxalylchloride, 3) Et₃N

3: 82 percent / tetrahydrofuran / Ambient temperature

With Chloro-oxo-acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

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) → (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 (128042-03-5)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 2) DMSO, oxalylchloride, 3) Et₃N

3: 82 percent / tetrahydrofuran / Ambient temperature

4: 70 percent / 9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 1 h / Ambient temperature

5: 87 percent / pyridinium chlorochromate, Celite, NaOAc, Florisil / CH₂Cl₂ / 1 h / Ambient temperature

With florisil; 9-borabicyclo[3.3.1]nonane dimer; Chloro-oxo-acetic acid; Celite; sodium acetate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

upstream raw materials:

[(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

chloromethyl methyl ether

Downstream raw materials:

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

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

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

(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