(2S,3R,4S)-3-Benzyloxy-2-hydroxy-2-methyl-4-((2R,3R,4S,4aS,5S,6S,8aS)-4,5,6-tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-pentanal

Base Information

• Chemical Name: (2S,3R,4S)-3-Benzyloxy-2-hydroxy-2-methyl-4-((2R,3R,4S,4aS,5S,6S,8aS)-4,5,6-tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-pentanal
• CAS No.: 128041-94-1
• Molecular Formula: C₄₆H₅₆O₁₀
• Molecular Weight: 768.945
• Mol file: 128041-94-1.mol

Synonyms:

Chemical Property of (2S,3R,4S)-3-Benzyloxy-2-hydroxy-2-methyl-4-((2R,3R,4S,4aS,5S,6S,8aS)-4,5,6-tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-pentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-3-Benzyloxy-2-hydroxy-2-methyl-4-((2R,3R,4S,4aS,5S,6S,8aS)-4,5,6-tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-pentanal

There total 19 articles about (2S,3R,4S)-3-Benzyloxy-2-hydroxy-2-methyl-4-((2R,3R,4S,4aS,5S,6S,8aS)-4,5,6-tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-pentanal 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) → (2S,3R,4S)-3-Benzyloxy-2-hydroxy-2-methyl-4-((2R,3R,4S,4aS,5S,6S,8aS)-4,5,6-tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-pentanal (128041-94-1)

Guidance literature:

Multi-step reaction with 9 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

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

7: 80 percent / 1) O₃, 2) Me₂S / CH₂Cl₂

8: 72 percent / tetrahydrofuran / -78 °C

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

With methanol; 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; dichloromethane;

Reference yield:

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 (128042-00-2) → (2S,3R,4S)-3-Benzyloxy-2-hydroxy-2-methyl-4-((2R,3R,4S,4aS,5S,6S,8aS)-4,5,6-tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-pentanal (128041-94-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / tetrahydrofuran / Ambient temperature

2: 70 percent / 9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 1 h / Ambient temperature

3: 87 percent / pyridinium chlorochromate, Celite, NaOAc, Florisil / CH₂Cl₂ / 1 h / Ambient temperature

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

5: 80 percent / 1) O₃, 2) Me₂S / CH₂Cl₂

6: 72 percent / tetrahydrofuran / -78 °C

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

With methanol; florisil; 9-borabicyclo[3.3.1]nonane dimer; dimethylsulfide; Celite; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

Reference yield:

(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) → (2S,3R,4S)-3-Benzyloxy-2-hydroxy-2-methyl-4-((2R,3R,4S,4aS,5S,6S,8aS)-4,5,6-tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-pentanal (128041-94-1)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 72 percent / tetrahydrofuran / -78 °C

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

With methanol; dimethylsulfide; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(3R,4R,5S)-4-Benzyloxy-3-methyl-5-((2R,3R,4S,4aS,5S,6S,8aS)-4,5,6-tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-hex-1-en-3-ol

((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

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-4,6,9-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

Downstream raw materials:

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