(S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol

Base Information

• Chemical Name: (S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol
• CAS No.: 182413-71-4
• Molecular Formula: C₃₁H₃₆O₆
• Molecular Weight: 504.623
• Mol file: 182413-71-4.mol

Synonyms:(S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol

Chemical Property of (S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol

There total 1 articles about (S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol 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: 75.0%

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) + allyl bromide (106-95-6) → (R)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol + (S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol (182413-71-4)

Guidance literature:

With tin; In water; acetonitrile; for 16h; usltasound;

DOI:10.1021/jo001447t

Reference yield: 97.0%

benzyl bromide (100-39-0) + (S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol (182413-71-4) → methyl 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-gluco-non-8-eno-pyranoside (182413-57-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; at 20 ℃; for 16h;

DOI:10.1021/jo001447t

Reference yield:

(S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol (182413-71-4) → (4S,8R,9R,10S)-4,8,9,10-Tetrakis-benzyloxy-1,6-dioxa-spiro[4.5]decane-2,7-diol

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / NaH; n-Bu₄NI / 16 h / 20 °C

2.1: IDCP / CH₂Cl₂ / 1 h / 20 °C

3.1: 2.1 g / Zn powder / aq. ethanol / 1 h / Heating

4.1: 95 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: O₃ / CH₂Cl₂; methanol / -78 °C

5.2: 95 percent / Ph₃P / methanol / 1 h

6.1: 9M HCl / tetrahydrofuran / 1 h / 20 °C

With hydrogenchloride; oxalyl dichloride; iodonium(di-γ-collidine) perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; 4.1: Swern oxidation;

DOI:10.1021/jo001447t

upstream raw materials:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

allyl bromide

Downstream raw materials:

methyl 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-gluco-non-8-eno-pyranoside

7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal

(4S,6S,7R,8R)-4,6,7,8-Tetrakis-benzyloxy-9,9-dimethoxy-non-1-en-5-one

(3S,5S,6R,7R)-3,5,6,7-Tetrakis-benzyloxy-8,8-dimethoxy-4-oxo-octanal