Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester
CAS No.:138624-49-4
Molecular Formula:C₅₄H₅₅NO₁₄S
Molecular Weight:974.095
Hs Code.:

Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

There total 13 articles about Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 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:

: 333-20-0
potassium thioacyanate

: Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R)-3,4-diacetoxy-5-benzyloxy-6-bromo-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

: 138624-49-4
Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With 18-crown-6 ether; In acetone; at 20 ℃; for 10h; Yield given;
DOI:10.1016/S0040-4039(00)74137-2

Reference yield:

: 29741-69-3
3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide

: 138624-49-4
Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: MeONa / methanol / 1 h / 20 °C

2: pyridine / 1. ) reflux, 2. ) 20 deg, 16 h

3: 85 percent / pyridine / 3 h / 20 °C

4: 82 percent / triphenylmethylium perchlorate / CH₂Cl₂ / 4 h

5: MeONa / methanol

6: pyridine / 1. ) reflux, 2. ) 20 deg, 16 h

7: pyridine / 3 h / 20 °C

8: 1.) Br₂, 2.) 18-crown-6 / 1.) CH₂Cl₂, 40 min, 2.) acetone, 20 deg C, 9.5 h

With pyridine; 18-crown-6 ether; bromine; sodium methylate; triphenylmethyl perchlorate; In methanol; dichloromethane;

Reference yield:

: (2R,3S,4S,5R,6S)-5-Benzyloxy-6-ethylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

: 138624-49-4
Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / pyridine / 3 h / 20 °C

2: 82 percent / triphenylmethylium perchlorate / CH₂Cl₂ / 4 h

3: MeONa / methanol

4: pyridine / 1. ) reflux, 2. ) 20 deg, 16 h

5: pyridine / 3 h / 20 °C

6: 1.) Br₂, 2.) 18-crown-6 / 1.) CH₂Cl₂, 40 min, 2.) acetone, 20 deg C, 9.5 h

With pyridine; 18-crown-6 ether; bromine; sodium methylate; triphenylmethyl perchlorate; In methanol; dichloromethane;